Tert-butyl 3-aminoazetidine-1-carboxylate → HCID 25254000, 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 1-N—Boc 3-amino azetidine. 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) and the final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.28 (m, 1 H) 1.33-1.46 (m, 2 H) 1.59-1.66 (m, 2 H) 1.75-1.87 (m, 4 H) 3.32 (s, 3 H) 3.67-3.80 (m, 4 H) 3.95 (s, 3 H) 4.07 (t, 2 H) 4.4-4.5 (m, 1 H) 4.65-4.83 (m, 1 H) 7.50 (d, J=8.3 Hz, 1 H) 7.54 (d, J=1.5 Hz, 1 H) 7.93 (s, 1 H) 8.21 (s, 1 H) 8.29 (d, J=8.1 Hz, 1 H) 8.81 (d, J=6.8 Hz, 1 H). [M+H] calc'd for C25H31F2N7O3 516; found 516.

Provenance & Evidence