Compound characterization data — Lepper et al., 2026

Stephan Lepper, Lukas Biermann, Emma C. Martens, Irina Honin, Alexandra Hamacher, Linda Schäker-Hübner, Matthias U. Kassack, Finn K. Hansen. “Aminoanilide-based class I HDAC PROTACs reveal distinct requirements for HDAC inhibition and targeted protein degradation: discovery of a mixed class I HDAC inhibitor/degrader with selective anticancer activity.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007556/v1

N-(2-Aminophenyl)-4-((1-(2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)amino)ethoxy)ethoxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide 2,2,2-trifluoroacetate
Identifier	1a
¹H NMR (600 MHz, DMSO-d₆)	δ 11.06 (s, 1H), 9.54 (s, 1H), 8.20 (s, 1H), 7.99 – 7.92 (m, 2H), 7.55 (d, J = 10.2 Hz, 1H), 7.20 (d, J = 7.2 Hz, 1H), 7.16 (dd, J = 7.9, 1.5 Hz, 1H), 7.14 – 7.11 (m, 2H), 6.97 (td, J = 7.6, 1.5 Hz, 1H), 6.79 (ddd, J = 13.0, 7.1, 2.1 Hz, 2H), 6.62 (td, J = 7.5, 1.4 Hz, 1H), 5.22 (s, 2H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 4.52 (t, J = 5.2 Hz, 2H), 3.82 (t, J = 5.2 Hz, 2H), 3.57 (t, J = 5.6 Hz, 2H), 3.52 (hept, J = 2.6 Hz, 4H), 3.44 (q, J = 5.6 Hz, 2H), 2.87 (ddd, J = 17.0, 13.9, 5.4 Hz, 1H), 2.57 (dt, J = 17.0, 3.2 Hz, 1H), 2.53 (d, J = 13.0 Hz, 1H), 2.01 (dtd, J = 13.0, 5.4, 2.3 Hz, 1H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.0, 167.1, 166.6, 164.7, 160.5, 153.8, 152.2, 142.9, 142.2, 129.8, 129.6, 127.0, 126.7, 126.3, 125.0, 123.8, 116.6, 116.5, 116.4, 114.2, 109.9, 105.6, 69.6, 69.5, 68.9, 68.7, 61.2, 49.4, 48.8, 42.2, 31.0, 22.2
HPLC	tR = 10.95 min (98.2 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₃₅H₃₅FN₈O₈: 715.2635, found: 715.2617

N-(2-Aminophenyl)-4-((1-(2-(2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)amino)ethoxy)ethoxy)ethoxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide bis(2,2,2-trifluoroacetate)
Identifier	1b
¹H NMR (600 MHz, DMSO-d₆)	δ 11.06 (s, 1H), 9.93 (s, 1H), 8.21 (s, 1H), 8.02 – 7.95 (m, 2H), 7.56 (d, J = 10.2 Hz, 1H), 7.32 – 7.28 (m, 1H), 7.23 – 7.11 (m, 4H), 7.09 (d, J = 8.0 Hz, 1H), 7.00 (t, J = 7.8 Hz, 1H), 6.78 (s, 1H), 5.23 (s, 2H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 4.53 (t, J = 5.2 Hz, 2H), 3.80 (q, J = 6.2 Hz, 2H), 3.67 – 3.57 (m, 2H), 3.55 – 3.40 (m, 10H), 2.87 (ddd, J = 17.1, 13.8, 5.4 Hz, 1H), 2.58 (dt, J = 17.1, 3.3 Hz, 1H), 2.55 – 2.51 (m, 1H), 2.04 – 1.97 (m, 1H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.0, 167.1, 166.6, 165.0, 160.8, 153.8, 152.2, 142.9, 142.8, 142.1, 129.8, 129.8, 126.7, 126.6, 126.4, 125.0, 116.5, 116.5, 114.3, 109.9, 109.8, 105.5, 69.8, 69.7, 69.6, 69.5, 68.9, 68.6, 61.3, 49.4, 48.8, 42.2, 31.0, 22.2
HPLC	tR = 15.54 min (98.2 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₃₇H₃₉FN₈O₉: 759.2897, found: 759.2897

N-(2-Aminophenyl)-4-((1-(8-((2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)amino)octyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide 2,2,2-trifluoroacetate
Identifier	1c
¹H NMR (600 MHz, DMSO-d₆)	δ 11.06 (s, 1H), 9.88 (s, 1H), 8.26 (s, 1H), 8.02 – 7.94 (m, 2H), 7.55 (d, J = 10.3 Hz, 1H), 7.28 (dd, J = 7.9, 1.5 Hz, 1H), 7.19 – 7.16 (m, 2H), 7.14 (td, J = 7.6, 1.5 Hz, 1H), 7.09 (d, J = 7.2 Hz, 1H), 7.05 (d, J = 7.4 Hz, 1H), 6.95 (t, J = 7.6 Hz, 1H), 6.87 (s, 1H), 5.24 (s, 2H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 4.36 (t, J = 7.1 Hz, 2H), 3.25 (t, J = 7.2 Hz, 2H), 2.87 (ddd, J = 17.0, 13.9, 5.4 Hz, 1H), 2.58 (ddd, J = 17.2, 4.2, 2.1 Hz, 1H), 2.54 (d, J = 13.1 Hz, 1H), 2.01 (dtd, J = 12.9, 5.4, 2.3 Hz, 1H), 1.82 (p, J = 7.2 Hz, 2H), 1.57 (p, J = 7.1 Hz, 2H), 1.36 – 1.20 (m, 8H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.1, 167.2, 166.7, 165.0, 160.7, 153.8, 152.2, 142.9, 142.2, 130.0, 129.8, 126.7, 126.5, 126.5, 124.5, 119.4, 116.1, 114.3, 109.9, 109.7, 104.9, 104.9, 61.3, 49.4, 48.8, 42.2, 31.0, 29.6, 28.6, 28.3, 28.0, 26.3, 25.8, 22.2
HPLC	tR = 11.58 min (97.2 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₃₇H₃₉FN₈O₆: 711.3049, found: 711.3040

N-(2-Aminophenyl)-4-((1-(2-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl)piperazin-1-yl)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide bis(2,2,2-trifluoroacetate)
Identifier	1d
¹H NMR (600 MHz, DMSO-d₆)	δ 11.10 (s, 1H), 9.78 (s, 1H), 8.14 (s, 1H), 7.99 (d, J = 8.7 Hz, 2H), 7.73 (d, J = 11.3 Hz, 1H), 7.48 (d, J = 7.3 Hz, 1H), 7.27 – 7.22 (m, 1H), 7.21 – 7.17 (m, 2H), 7.11 – 7.06 (m, 1H), 6.97 (d, J = 8.0 Hz, 1H), 6.84 (t, J = 7.6 Hz, 1H), 5.59 (d, J = 41.4 Hz, 2H), 5.28 (s, 2H), 5.11 (dd, J = 12.9, 5.4 Hz, 1H), 4.37 (s, 1H), 4.11 (s, 1H), 3.63 (t, J = 24.0 Hz, 5H), 3.13 (d, J = 6.8 Hz, 5H), 2.94 (t, J = 12.2 Hz, 2H), 2.91 – 2.85 (m, 1H), 2.60 (dt, J = 17.4, 3.5 Hz, 1H), 2.55 (dd, J = 13.1, 4.5 Hz, 1H), 2.05 (dddd, J = 17.9, 12.6, 8.4, 5.0 Hz, 2H), 1.95 – 1.86 (m, 2H), 1.41 (qd, J = 12.5, 3.9 Hz, 2H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 169.9, 166.7, 166.2, 164.9, 164.6, 160.7, 156.4, 145.5, 142.1, 129.7, 128.8, 126.7, 126.4, 125.8, 123.1, 119.5, 118.3, 117.4, 115.5, 114.3, 113.9, 112.0, 111.9, 61.2, 60.8, 51.4, 51.1, 50.5, 49.3, 49.1, 30.9, 30.0, 29.2, 22.1
HPLC	tR = 10.58 min (99.1 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₄₁H₄₃FN₁₀O₇: 807.3373, found: 807.3375

N-(2-Aminophenyl)-4-((1-(2-(4-(1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)piperazin-1-yl)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide tris(2,2,2-trifluoroacetate)
Identifier	1e
¹H NMR (600 MHz, DMSO-d₆)	δ 11.10 (s, 1H), 9.84 (s, 1H), 8.13 (s, 1H), 8.00 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 11.1 Hz, 1H), 7.52 (d, J = 7.3 Hz, 1H), 7.27 (d, J = 7.8 Hz, 1H), 7.19 (d, J = 8.5 Hz, 2H), 7.11 (t, J = 7.6 Hz, 1H), 7.01 (d, J = 7.9 Hz, 1H), 6.89 (t, J = 7.6 Hz, 1H), 5.58 (s, 2H), 5.28 (s, 2H), 5.11 (dd, J = 12.9, 5.4 Hz, 1H), 4.31 (d, J = 174.1 Hz, 5H), 3.79 (d, J = 12.1 Hz, 2H), 3.53 (td, J = 11.7, 6.1 Hz, 2H), 3.09 (s, 2H), 2.98 (t, J = 12.3 Hz, 2H), 2.89 (ddd, J = 16.8, 13.8, 5.5 Hz, 1H), 2.60 (dt, J = 17.0, 3.5 Hz, 1H), 2.58 – 2.51 (m, 1H), 2.18 (d, J = 11.5 Hz, 2H), 2.04 (ddd, J = 10.8, 6.5, 3.9 Hz, 1H), 1.90 – 1.77 (m, 2H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 169.9, 166.6, 166.1, 164.9, 164.6, 160.7, 156.5, 144.7, 144.6, 142.1, 129.8, 128.7, 126.7, 126.6, 126.5, 126.4, 123.8, 123.7, 120.4, 118.8, 114.3, 112.1, 111.9, 62.1, 61.2, 50.6, 49.1, 48.4, 47.8, 41.5, 30.9, 25.9, 22.0
HPLC	tR = 10.55 min (95.2 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₄₀H₄₁FN₁₀O₇: 793.3216, found: 793.3220

N-(2-Amino-5-(pyridin-4-yl)phenyl)-4-((1-(2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)amino)ethoxy)ethoxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide bis(2,2,2-trifluoroacetate)
Identifier	2a
¹H NMR (600 MHz, DMSO-d₆)	δ 11.06 (s, 1H), 9.62 (s, 1H), 8.70 (d, J = 6.5 Hz, 2H), 8.22 (s, 1H), 8.20 – 8.16 (m, 2H), 8.00 (d, J = 8.7 Hz, 2H), 7.95 (d, J = 2.3 Hz, 1H), 7.79 (dd, J = 8.6, 2.3 Hz, 1H), 7.55 (d, J = 10.2 Hz, 1H), 7.20 (d, J = 7.2 Hz, 1H), 7.17 – 7.13 (m, 2H), 6.93 (d, J = 8.6 Hz, 1H), 6.79 (s, 1H), 5.23 (s, 2H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 4.53 (t, J = 5.2 Hz, 2H), 3.82 (t, J = 5.2 Hz, 2H), 3.58 (t, J = 5.6 Hz, 2H), 3.53 (s, 4H), 3.44 (q, J = 5.1 Hz, 2H), 2.87 (ddd, J = 17.0, 13.8, 5.5 Hz, 1H), 2.57 (dt, J = 17.1, 3.2 Hz, 1H), 2.51 (d, J = 5.7 Hz, 1H), 2.06 – 1.97 (m, 1H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.1, 167.1, 166.6, 165.3, 160.6, 154.7, 153.8, 152.2, 148.2, 142.8, 142.2, 141.6, 129.8, 127.5, 127.0, 126.8, 125.0, 123.4, 120.6, 120.0, 116.5, 115.8, 114.2, 109.8, 105.6, 69.6, 69.5, 68.9, 68.7, 61.2, 49.4, 48.9, 42.2, 31.0, 22.2
HPLC	tR = 10.74 min (98.1 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₄₀H₃₈FN₉O₈: 792.2900, found: 792.2905

N-(2-Amino-5-(pyridin-4-yl)phenyl)-4-((1-(2-(2-(2-(2-((2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)amino)ethoxy)ethoxy)ethoxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide bis(2,2,2-trifluoroacetate)
Identifier	2b
¹H NMR (600 MHz, DMSO-d₆)	δ 11.06 (s, 1H), 9.62 (s, 1H), 8.72 – 8.66 (m, 2H), 8.22 (s, 1H), 8.19 – 8.16 (m, 2H), 8.03 – 7.98 (m, 2H), 7.95 (d, J = 2.3 Hz, 1H), 7.79 (dd, J = 8.6, 2.3 Hz, 1H), 7.55 (d, J = 10.2 Hz, 1H), 7.20 (d, J = 7.2 Hz, 1H), 7.18 – 7.14 (m, 2H), 6.93 (d, J = 8.6 Hz, 1H), 6.78 (s, 1H), 5.23 (s, 2H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 4.53 (t, J = 5.2 Hz, 2H), 3.81 (t, J = 5.2 Hz, 2H), 3.59 (t, J = 5.6 Hz, 2H), 3.54 – 3.49 (m, 4H), 3.44 (s, 6H), 2.87 (ddd, J = 17.1, 13.8, 5.4 Hz, 1H), 2.57 (dt, J = 17.0, 3.1 Hz, 1H), 2.53 (d, J = 15.4 Hz, 1H), 2.00 (dtd, J = 12.8, 5.3, 2.3 Hz, 1H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.0, 167.1, 166.6, 165.3, 160.6, 154.6, 153.8, 152.2, 148.1, 142.9, 142.1, 141.7, 129.8, 127.4, 126.9, 126.8, 125.0, 123.4, 120.6, 120.1, 116.5, 115.8, 114.2, 109.9, 105.6, 69.8, 69.7, 69.6, 69.5, 68.9, 68.6, 61.3, 49.4, 48.8, 42.2, 31.0, 22.2
HPLC	tR = 10.73 min (95.0 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₄₂H₄₂FN₉O₉: 836.3162, found: 836.3165

N-(2-Amino-5-(pyridin-4-yl)phenyl)-4-((1-(8-((2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)amino)octyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide bis(2,2,2-trifluoroacetate)
Identifier	2c
¹H NMR (600 MHz, DMSO-d₆)	δ 11.06 (s, 1H), 9.62 (s, 1H), 8.69 (d, J = 6.3 Hz, 2H), 8.27 (s, 1H), 8.19 – 8.12 (m, 2H), 8.01 (d, J = 8.6 Hz, 2H), 7.94 (d, J = 2.3 Hz, 1H), 7.78 (dd, J = 8.6, 2.3 Hz, 1H), 7.54 (d, J = 10.2 Hz, 1H), 7.16 (d, J = 8.6 Hz, 2H), 7.08 (d, J = 7.1 Hz, 1H), 6.92 (d, J = 8.6 Hz, 1H), 6.87 (s, 1H), 5.24 (s, 2H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 4.37 (t, J = 7.1 Hz, 2H), 3.24 (s, 2H), 2.87 (ddd, J = 17.0, 13.9, 5.4 Hz, 1H), 2.58 (dt, J = 17.1, 3.3 Hz, 1H), 2.54 (d, J = 13.1 Hz, 1H), 2.05 – 1.97 (m, 1H), 1.82 (p, J = 7.2 Hz, 2H), 1.57 (p, J = 7.0 Hz, 2H), 1.38 – 1.20 (m, 8H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.1, 167.2, 166.6, 165.3, 160.6, 154.5, 153.8, 152.2, 148.1, 142.9, 142.2, 141.9, 130.0, 129.8, 127.4, 126.8, 124.5, 123.4, 120.5, 120.1, 116.1, 115.8, 114.2, 109.9, 104.9, 61.3, 49.4, 48.8, 42.2, 31.0, 29.7, 28.6, 28.3, 28.0, 26.3, 25.8, 22.2
HPLC	tR = 11.13 min (96.1 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₄₂H₄₂FN₉O₆: 788.3315, found: 788.3323

N-(2-Amino-5-(pyridin-4-yl)phenyl)-4-((1-(2-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl)piperazin-1-yl)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide tris(2,2,2-trifluoroacetate)
Identifier	2d
¹H NMR (600 MHz, DMSO-d₆)	δ 11.10 (s, 1H), 9.64 (s, 1H), 8.69 (d, J = 6.2 Hz, 2H), 8.20 – 8.13 (m, 3H), 8.03 (d, J = 8.5 Hz, 2H), 7.95 (d, J = 2.3 Hz, 1H), 7.79 (dd, J = 8.6, 2.3 Hz, 1H), 7.73 (d, J = 11.3 Hz, 1H), 7.47 (d, J = 7.3 Hz, 1H), 7.22 – 7.18 (m, 2H), 6.93 (d, J = 8.6 Hz, 1H), 5.60 (s, 2H), 5.28 (s, 2H), 5.11 (dd, J = 12.9, 5.4 Hz, 1H), 4.34 (s, 1H), 4.08 (s, 2H), 3.81 – 3.43 (m, 5H), 3.12 (d, J = 6.8 Hz, 4H), 2.98 – 2.84 (m, 3H), 2.63 – 2.50 (m, 2H), 2.12 – 2.00 (m, 2H), 1.95 – 1.87 (m, 2H), 1.41 (qd, J = 12.5, 3.8 Hz, 2H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 169.9, 166.7, 166.2, 165.2, 164.6, 160.7, 156.4, 154.4, 148.0, 145.5, 142.1, 141.9, 129.8, 128.8, 127.4, 126.8, 126.4, 123.4, 123.2, 120.5, 120.2, 115.8, 114.2, 113.9, 112.0, 111.9, 61.2, 60.8, 51.4, 50.6, 49.3, 49.1, 30.9, 30.0, 29.2, 25.5, 22.1
HPLC	tR = 13.66 min (95.0 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₄₆H₄₆FN₁₁O₇: 884.3638, found: 884.3636

N-(2-Amino-5-(pyridin-4-yl)phenyl)-4-((1-(2-(4-(1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)piperazin-1-yl)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methoxy)benzamide bis(2,2,2-trifluoroacetate)
Identifier	2e
¹H NMR (600 MHz, DMSO-d₆)	δ 11.10 (s, 1H), 9.65 (s, 1H), 8.69 (d, J = 6.2 Hz, 2H), 8.20 – 8.12 (m, 3H), 8.03 (d, J = 8.5 Hz, 2H), 7.95 (d, J = 2.3 Hz, 1H), 7.83 – 7.72 (m, 2H), 7.52 (d, J = 7.3 Hz, 1H), 7.24 – 7.14 (m, 2H), 6.93 (d, J = 8.6 Hz, 1H), 5.59 (s, 2H), 5.28 (s, 2H), 5.11 (dd, J = 12.9, 5.4 Hz, 1H), 4.43 (s, 1H), 4.11 (s, 2H), 3.79 (d, J = 12.0 Hz, 3H), 3.52 (td, J = 11.5, 6.1 Hz, 5H), 2.98 (s, 2H), 2.89 (ddd, J = 17.1, 13.8, 5.5 Hz, 1H), 2.64 – 2.51 (m, 2H), 2.23 – 2.12 (m, 2H), 2.04 (tt, J = 7.9, 4.3 Hz, 1H), 1.84 (td, J = 12.4, 8.6 Hz, 2H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 169.8, 166.6, 166.1, 165.3, 164.6, 160.7, 156.5, 154.4, 148.0, 144.6, 142.1, 142.0, 129.8, 128.7, 127.4, 126.8, 126.4, 123.7, 123.7, 123.4, 120.5, 120.2, 115.9, 114.2, 112.1, 111.9, 62.1, 61.2, 50.6, 49.1, 48.4, 47.7, 41.5, 30.9, 25.9, 22.0
HPLC	tR = 10.52 min (98.5 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₄₅H₄₄FN₁₁O₇: 870.3482, found: 870.3483

(2S,4R)-1-((S)-14-(4-((4-((2-Amino-5-(pyridin-4-yl)phenyl)carbamoyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)-2-(tert-butyl)-4-oxo-6,9,12-trioxa-3-azatetradecanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide bis(2,2,2-trifluoroacetate)
Identifier	2f
¹H NMR (600 MHz, DMSO-d₆)	δ 9.62 (s, 1H), 8.98 (d, J = 8.7 Hz, 1H), 8.70 (d, J = 6.3 Hz, 2H), 8.57 (t, J = 6.1 Hz, 1H), 8.22 (s, 1H), 8.21 – 8.16 (m, 2H), 8.05 – 8.00 (m, 2H), 7.96 (d, J = 2.3 Hz, 1H), 7.80 (dd, J = 8.7, 2.3 Hz, 1H), 7.40 (d, J = 7.3 Hz, 5H), 7.20 – 7.14 (m, 2H), 6.93 (d, J = 8.6 Hz, 1H), 5.24 (s, 2H), 4.57 (dd, J = 9.6, 2.4 Hz, 1H), 4.55 – 4.53 (m, 2H), 4.44 (q, J = 7.7 Hz, 2H), 4.41 – 4.33 (m, 3H), 4.26 (dt, J = 15.7, 5.9 Hz, 2H), 3.96 (s, 2H), 3.82 (t, J = 5.2 Hz, 2H), 3.67 (dt, J = 10.6, 4.0 Hz, 1H), 3.62 – 3.57 (m, 5H), 2.96 (s, 1H), 2.44 (s, 3H), 2.06 (ddt, J = 12.5, 7.7, 1.9 Hz, 1H), 1.90 (ddd, J = 12.9, 8.7, 4.5 Hz, 1H), 0.95 (d, J = 6.0 Hz, 10H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 171.7, 169.1, 168.6, 165.3, 160.7, 159.5, 154.9, 151.4, 148.2, 147.7, 142.1, 141.5, 139.4, 131.1, 129.8, 129.7, 128.7, 127.5, 127.0, 126.8, 125.1, 123.4, 120.6, 119.9, 115.8, 114.2, 70.4, 69.6, 68.8, 68.7, 61.3, 58.7, 56.5, 55.7, 49.4, 48.9, 43.4, 41.7, 37.9, 35.7, 34.3, 26.2, 15.9
HPLC	tR = 10.65 min (97.5 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₅₁H₆₀N₁₀O₉S: 989.4338, found: 989.4339

(2S,4R)-1-((S)-2-(8-(4-((4-((2-Amino-5-(pyridin-4-yl)phenyl)carbamoyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)octanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide bis(2,2,2-trifluoroacetate)
Identifier	2g
¹H NMR (600 MHz, DMSO-d₆)	δ 9.63 (s, 1H), 8.98 (s, 1H), 8.69 (d, J = 6.4 Hz, 2H), 8.54 (t, J = 6.1 Hz, 1H), 8.26 (s, 1H), 8.18 (d, J = 6.4 Hz, 2H), 8.01 (d, J = 8.5 Hz, 2H), 7.95 (d, J = 2.3 Hz, 1H), 7.80 (ddd, J = 11.0, 9.0, 2.8 Hz, 2H), 7.48 – 7.35 (m, 4H), 7.17 (d, J = 8.6 Hz, 2H), 6.93 (d, J = 8.6 Hz, 1H), 5.24 (s, 2H), 4.54 (d, J = 9.3 Hz, 1H), 4.46 – 4.40 (m, 2H), 4.36 (q, J = 5.8 Hz, 3H), 4.22 (dd, J = 15.8, 5.5 Hz, 1H), 3.72 – 3.61 (m, 2H), 2.44 (s, 3H), 2.26 (dt, J = 14.7, 7.6 Hz, 1H), 2.11 (ddd, J = 14.2, 8.1, 6.3 Hz, 1H), 2.06 – 2.00 (m, 1H), 1.91 (ddd, J = 13.0, 8.5, 4.6 Hz, 1H), 1.81 (p, J = 7.2 Hz, 2H), 1.47 (dtq, J = 27.7, 13.9, 7.4 Hz, 2H), 1.29 (dt, J = 10.4, 6.4 Hz, 2H), 1.22 (p, J = 7.3 Hz, 4H), 0.93 (s, 10H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.0, 171.9, 169.7, 165.3, 160.6, 154.7, 151.4, 148.2, 147.7, 142.2, 141.7, 139.5, 131.1, 129.8, 129.6, 128.6, 127.5, 127.4, 127.0, 126.8, 124.5, 123.4, 120.6, 120.0, 115.8, 114.2, 68.8, 61.3, 58.7, 56.3, 49.4, 41.6, 37.9, 35.2, 34.8, 29.7, 28.4, 28.0, 26.7, 26.4, 25.7, 25.3, 15.9
HPLC	tR = 10.83 min (98.6 % purity)
HR-MS (ESI)	m/z: [M+H]⁺ calcd for C₅₁H₆₀N₁₀O₆S: 941.4491, found: 941.4490

tert-Butyl (4-bromo-2-nitrophenyl)carbamate
Identifier	4
¹H NMR (500 MHz, DMSO-d₆)	δ 9.66 (s, 1H), 8.12 (dd, J = 2.4, 0.9 Hz, 1H), 7.86 (ddd, J = 8.8, 2.5, 0.9 Hz, 1H), 7.60 (d, J = 8.8 Hz, 1H), 1.44 (d, J = 0.9 Hz, 9H)
¹³C NMR (126 MHz, DMSO-d₆)	δ 152.1, 141.4, 136.7, 132.0, 127.4, 125.6, 114.7, 80.8, 27.8
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₁₁H₁₃BrN₂O₄: 317.0, found: 317.1

tert-Butyl (2-nitro-4-(pyridin-4-yl)phenyl)carbamate
Identifier	5
¹H NMR (500 MHz, DMSO-d₆)	δ 9.74 (s, 1H), 8.78 – 8.57 (m, 2H), 8.35 (d, J = 2.2 Hz, 1H), 8.13 (dd, J = 8.6, 2.3 Hz, 1H), 7.82 (d, J = 8.6 Hz, 1H), 7.80 – 7.76 (m, 2H), 1.47 (s, 9H)
¹³C NMR (126 MHz, DMSO-d₆)	δ 152.2, 150.4, 144.3, 141.2, 133.2, 132.4, 132.1, 124.2, 123.3, 120.9, 80.8, 27.8
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₁₆H₁₇N₃O₄: 316.1, found: 316.4

tert-Butyl (2-amino-4-(pyridin-4-yl)phenyl)carbamate
Identifier	6
¹H NMR (500 MHz, DMSO-d₆)	δ 8.61 – 8.54 (m, 2H), 8.41 (s, 1H), 7.57 – 7.53 (m, 2H), 7.42 (d, J = 8.3 Hz, 1H), 7.11 (d, J = 2.2 Hz, 1H), 6.98 (dd, J = 8.3, 2.2 Hz, 1H), 5.06 (s, 2H), 1.48 (s, 9H)
¹³C NMR (126 MHz, DMSO-d₆)	δ 153.3, 150.0, 147.2, 141.0, 133.1, 125.1, 124.1, 120.6, 114.7, 113.5, 78.9, 28.1
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₁₆H₁₉N₃O₂: 286.2, found: 286.1

tert-Butyl (2-(4-(prop-2-yn-1-yloxy)benzamido)phenyl)carbamate
Identifier	8
¹H NMR (600 MHz, DMSO-d₆)	δ 9.73 (s, 1H), 8.62 (s, 1H), 8.00 – 7.90 (m, 2H), 7.53 (ddd, J = 9.9, 8.1, 1.6 Hz, 2H), 7.19 (td, J = 7.7, 1.6 Hz, 1H), 7.16 – 7.11 (m, 3H), 4.91 (d, J = 2.4 Hz, 2H), 3.61 (t, J = 2.4 Hz, 1H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 164.7, 159.9, 153.4, 131.7, 129.8, 129.4, 127.8, 127.1, 126.0, 125.4, 124.0, 123.8, 123.4, 114.6, 79.6, 78.8, 78.6, 55.6, 28.0
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₁H₂₂N₂O₄: 367.2, found: 367.2

tert-Butyl (2-(4-(prop-2-yn-1-yloxy)benzamido)-4-(pyridin-4-yl)phenyl)carbamate
Identifier	9
¹H NMR (600 MHz, DMSO-d₆)	δ 9.85 (s, 1H), 8.81 (s, 1H), 8.64 – 8.60 (m, 2H), 8.01 – 7.97 (m, 2H), 7.96 (d, J = 2.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.69 – 7.66 (m, 3H), 7.17 – 7.13 (m, 2H), 4.92 (d, J = 2.4 Hz, 2H), 3.64 – 3.58 (m, 1H), 1.47 (s, 9H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 165.1, 160.0, 153.2, 150.3, 146.1, 133.1, 132.3, 129.9, 129.6, 127.0, 124.5, 123.9, 120.8, 114.6, 79.9, 78.8, 78.6, 55.7, 28.0
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₆H₂₃N₃O₄: 444.2, found: 444.2

5-((2-(2-(2-Azidoethoxy)ethoxy)ethyl)amino)-2-(2,6-dioxopiperidin-3-yl)-6-fluoroisoindoline-1,3-dione
Identifier	11
¹H NMR (600 MHz, DMSO-d₆)	δ 11.05 (s, 1H), 7.56 (d, J = 10.3 Hz, 1H), 7.21 (d, J = 7.2 Hz, 1H), 6.78 (td, J = 5.9, 2.9 Hz, 1H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 3.62 (t, J = 5.6 Hz, 2H), 3.60 – 3.54 (m, 6H), 3.47 (q, J = 5.7 Hz, 2H), 3.35 (dd, J = 5.6, 4.3 Hz, 2H), 2.93 – 2.84 (m, 1H), 2.58 (ddd, J = 17.1, 4.6, 2.4 Hz, 1H), 2.53 (d, J = 7.2 Hz, 1H), 2.01 (dtd, J = 12.9, 5.4, 2.3 Hz, 1H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.0, 167.1, 166.6, 152.2, 142.9, 129.8, 116.5, 109.9, 105.6, 69.8, 69.7, 69.3, 69.0, 50.0, 48.8, 42.2, 30.9, 22.2
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₁₉H₂₁FN₆O₆: 449.2, found: 449.3

5-((2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)ethyl)amino)-2-(2,6-dioxopiperidin-3-yl)-6-fluoroisoindoline-1,3-dione
Identifier	12
¹H NMR (600 MHz, DMSO-d₆)	δ 11.05 (s, 1H), 7.54 (dd, J = 33.3, 10.2 Hz, 1H), 7.19 (dd, J = 25.3, 7.1 Hz, 1H), 6.79 (q, J = 4.9 Hz, 1H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 3.61 (t, J = 5.6 Hz, 2H), 3.57 (t, J = 5.2 Hz, 3H), 3.52 (s, 5H), 3.46 (q, J = 5.6 Hz, 3H), 3.36 (t, J = 5.0 Hz, 3H), 2.88 (ddd, J = 18.1, 13.9, 5.4 Hz, 1H), 2.63 – 2.56 (m, 1H), 2.54 (d, J = 13.0 Hz, 1H), 2.01 (dt, J = 11.5, 5.4 Hz, 1H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.0, 167.1, 166.6, 152.2, 142.8, 129.8, 116.4, 109.9, 105.6, 69.8, 69.8, 69.7, 69.4, 69.2, 68.9, 50.0, 48.8, 42.2, 30.9, 22.2
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₁H₂₅FN₆O₇: 493.2, found: 493.3

5-((8-Azidooctyl)amino)-2-(2,6-dioxopiperidin-3-yl)-6-fluoroisoindoline-1,3-dione
Identifier	13
¹H NMR (600 MHz, DMSO-d₆)	δ 11.06 (d, J = 9.4 Hz, 1H), 7.55 (d, J = 10.1 Hz, 1H), 7.09 (d, J = 7.0 Hz, 1H), 6.88 (q, J = 4.2 Hz, 1H), 5.05 (dd, J = 12.9, 5.4 Hz, 1H), 3.29 (d, J = 4.8 Hz, 1H), 3.25 (q, J = 6.7 Hz, 2H), 2.94 – 2.83 (m, 2H), 2.66 – 2.55 (m, 2H), 2.12 – 1.96 (m, 2H), 1.55 (dp, J = 31.0, 7.0 Hz, 5H), 1.33 – 1.29 (m, 6H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 170.0, 167.1, 165.3, 152.2, 142.9, 130.0, 116.1, 113.8, 109.9, 50.6, 49.4, 48.8, 42.2, 30.9, 28.6, 28.2, 26.3, 26.1, 22.2, 21.9
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₁H₂₅FN₆O₄: 445.2, found: 445.4

tert-Butyl 4-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl)piperazine-1-carboxylate
Identifier	14i
¹H NMR (500 MHz, DMSO-d₆)	δ 11.08 (s, 1H), 7.69 (d, J = 11.4 Hz, 1H), 7.43 (d, J = 7.4 Hz, 1H), 5.09 (dd, J = 12.9, 5.4 Hz, 1H), 4.03 (q, J = 7.1 Hz, 1H), 3.59 (dd, J = 9.4, 6.3 Hz, 2H), 3.31 (d, J = 4.9 Hz, 3H), 2.88 (tt, J = 13.7, 3.6 Hz, 3H), 2.64 – 2.56 (m, 1H), 2.54 (t, J = 6.5 Hz, 1H), 2.30 (t, J = 5.0 Hz, 4H), 2.18 (d, J = 7.2 Hz, 2H), 2.03 (dtd, J = 11.7, 4.6, 2.0 Hz, 1H), 1.85 – 1.78 (m, 2H), 1.73 (tq, J = 7.2, 3.7 Hz, 1H), 1.39 (s, 9H), 1.32 – 1.20 (m, 2H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.7, 166.7, 166.2, 158.1, 156.4, 153.8, 145.8, 128.8, 122.7, 113.7, 111.9, 78.7, 63.7, 53.0, 49.9, 49.0, 42.1, 32.2, 30.9, 30.2, 28.0, 22.0
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₈H₃₆FN₅O₆: 558.3, found: 558.1

5-(4-((4-(2-Azidoacetyl)piperazin-1-yl)methyl)piperidin-1-yl)-2-(2,6-dioxopiperidin-3-yl)-6-fluoroisoindoline-1,3-dione
Identifier	14
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₅H₂₉FN₈O₅: 541.2, found: 541.0

tert-Butyl 4-(1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)piperazine-1-carboxylate
Identifier	15i
¹H NMR (500 MHz, DMSO-d₆)	δ 11.04 (s, 1H), 7.65 (d, J = 11.4 Hz, 1H), 7.40 (d, J = 7.4 Hz, 1H), 5.05 (ddd, J = 12.8, 5.4, 1.4 Hz, 1H), 3.61 (d, J = 11.9 Hz, 2H), 2.90 – 2.79 (m, 3H), 2.59 – 2.52 (m, 1H), 2.46 (p, J = 1.9 Hz, 6H), 2.42 (t, J = 5.1 Hz, 4H), 1.99 (dtd, J = 12.9, 5.2, 2.2 Hz, 1H), 1.85 – 1.77 (m, 2H), 1.52 (qd, J = 12.1, 3.9 Hz, 2H), 1.36 (s, 9H)
¹³C NMR (126 MHz, DMSO-d₆)	δ 172.7, 169.8, 166.6, 153.7, 145.5, 128.7, 123.0, 113.7, 111.9, 111.7, 78.6, 60.4, 49.3, 49.0, 48.5, 40.4, 30.9, 28.0, 27.7, 22.0
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₇H₃₄FN₅O₆: 544.3, found: 544.1

5-(4-(4-(2-Azidoacetyl)piperazin-1-yl)piperidin-1-yl)-2-(2,6-dioxopiperidin-3-yl)-6-fluoroisoindoline-1,3-dione
Identifier	15
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₂₄H₂₇FN₈O₅: 527.2, found: 527.1

(2S,4R)-1-((S)-14-Amino-2-(tert-butyl)-4-oxo-6,9,12-trioxa-3-azatetradecanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide dihydrochloride
Identifier	17i
¹H NMR (600 MHz, DMSO-d₆)	δ 9.03 (s, 1H), 8.63 (t, J = 6.1 Hz, 1H), 7.97 (d, J = 24.0 Hz, 2H), 7.47 – 7.43 (m, 1H), 7.40 (s, 4H), 4.57 (d, J = 9.3 Hz, 1H), 4.45 (t, J = 8.1 Hz, 1H), 4.41 – 4.34 (m, 2H), 4.27 (dd, J = 15.6, 5.6 Hz, 1H), 3.98 (s, 2H), 3.67 (dd, J = 10.5, 4.1 Hz, 1H), 3.62 (d, J = 5.6 Hz, 2H), 3.59 (d, J = 9.2 Hz, 8H), 2.99 – 2.90 (m, 2H), 2.45 (s, 3H), 2.07 (dd, J = 13.0, 7.9 Hz, 1H), 1.90 (ddd, J = 13.0, 8.9, 4.5 Hz, 1H), 1.36 – 1.20 (m, 1H), 0.95 (s, 10H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 171.7, 169.1, 168.6, 151.6, 147.5, 139.5, 131.3, 129.6, 128.7, 127.5, 70.4, 69.7, 69.5, 68.8, 66.6, 66.3, 58.7, 56.6, 55.7, 41.6, 38.5, 35.7, 26.2, 15.8
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₃₀H₄₅N₅O₇S: 620.3, found: 620.5

(2S,4R)-1-((S)-14-Azido-2-(tert-butyl)-4-oxo-6,9,12-trioxa-3-azatetradecanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Identifier	17
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₃₀H₄₃N₇O₇S: 646.3, found: 646.4

(2S,4R)-1-((S)-2-(8-Aminooctanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide dihydrochloride
Identifier	18i
¹H NMR (600 MHz, DMSO-d₆)	δ 9.03 (s, 1H), 8.57 (t, J = 6.1 Hz, 1H), 7.90 (s, 2H), 7.82 (d, J = 9.4 Hz, 1H), 7.50 – 7.36 (m, 4H), 4.54 (d, J = 9.4 Hz, 1H), 4.42 (ddd, J = 10.9, 6.6, 3.1 Hz, 2H), 4.35 (dp, J = 4.5, 2.4 Hz, 1H), 4.23 (d, J = 5.4 Hz, 1H), 3.72 – 3.60 (m, 2H), 2.73 (ddd, J = 11.7, 8.9, 6.0 Hz, 2H), 2.45 (s, 3H), 2.25 (dt, J = 14.8, 7.6 Hz, 1H), 2.12 (ddd, J = 14.3, 8.1, 6.4 Hz, 1H), 2.04 (ddt, J = 12.2, 8.0, 1.8 Hz, 1H), 1.90 (ddd, J = 12.9, 8.6, 4.7 Hz, 1H), 1.52 (dt, J = 10.1, 7.0 Hz, 3H), 1.46 (dt, J = 13.3, 7.1 Hz, 1H), 1.29 – 1.22 (m, 6H), 0.93 (s, 10H)
¹³C NMR (151 MHz, DMSO-d₆)	δ 172.0, 171.9, 169.7, 151.6, 147.4, 139.6, 131.3, 129.5, 128.6, 127.4, 68.8, 66.3, 58.7, 56.3, 41.6, 38.7, 37.9, 35.2, 34.8, 34.1, 28.4, 26.9, 26.4, 25.7, 25.3, 15.8
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₃₀H₄₅N₅O₄S: 572.3, found: 572.4

(2S,4R)-1-((S)-2-(8-Azidooctanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
Identifier	18
LR-MS (ESI)	m/z: [M+H]⁺ calcd for C₃₀H₄₃N₇O₄S: 598.3, found: 598.4