(R)-(+)-1-Boc-3-aminopyrrolidine → HCID 25254781, 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 (R)-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 1.11-1.27 (m, 1 H) 1.28-1.47 (m, 2 H) 1.52-1.71 (m, 4 H) 1.71-1.89 (m, 4 H) 1.89-2.04 (m, 1 H) 2.64 (dd, J=11.12, 5.05 Hz, 1 H) 2.75 (ddd, J=10.74, 7.96, 6.32 Hz, 1 H) 2.83-3.03 (m, 2 H) 3.31 (s, 3 H) 3.94 (s, 3 H) 4.06 (t, J=13.52 Hz, 2 H) 4.22-4.36 (m, 1 H) 4.38-4.54 (m, 1 H) 7.47 (dd, J=8.46, 1.64 Hz, 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: 195-198° C. [M+H] calc'd for C26H33F2N7O3 530; found 530.

Provenance & Evidence