tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate → HCID 25254780, compound

Participants

Reaction Steps

The title compound was synthesized from 4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and (S)-1-N—Boc 3-amino pyrrolidine. The final compound was purified by reverse phase HPLC and basified to give the free base. Further, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group was removed using 40% TFA in dichloromethane (6 ml). The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.28 (m, 1 H) 1.30-1.47 (m, 2 H) 1.51-1.72 (m, 4 H) 1.73-1.88 (m, 4 H) 1.90-2.06 (m, 1 H) 2.64 (dd, J=11.24, 4.93 Hz, 1 H) 2.75 (ddd, J=10.67, 7.89, 6.44 Hz, 1 H) 2.82-3.03 (m, 2 H) 3.31 (s, 3 H) 3.94 (s, 3 H) 4.06 (t, J=13.52 Hz, 2 H) 4.23-4.37 (m, 1 H) 4.39-4.53 (m, 1 H) 7.44-7.50 (m, 1 H) 7.51 (d, J=1.52 Hz, 1 H) 7.90 (s, 1 H) 8.21 (s, 1 H) 8.23 (d, J=7.07 Hz, 1 H) 8.26 (d, J=8.34 Hz, 1 H). Melting point: 258-263° C. [M+H] calc'd for C26H33F2N7O3 530; found 530.

Provenance & Evidence