4-Amino-1-Boc-piperidine → 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-(2-(pyrrolidin-1-yl)acetyl)piperidin-4-yl)benzamide

Participants

Reaction Steps

The title compound was synthesized from (R)-4-(9-cyclohexyl-7-fluoro-7-vinyl-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-Boc-4-aminopiperidine. Further, after washing with water (10 ml), t-butoxycarbonyl (Boc) protection group was removed using 40% TFA in dichloromethane (6 ml). The resulting product was further acylated using 2-(pyrrolidin-1-yl)acetyl chloride. The title product using preparative HPLC and neutralized with bicarbonate. 1H NMR (400 MHz, DMF) δ ppm 1.53-2.30 (m, 18 H) 2.79-3.01 (m, 2 H) 3.21-3.47 (m, 5 H) 4.17 (s, 3 H) 4.21-4.41 (m, 6 H) 4.59 (d, J=12.13 Hz, 1 H) 5.00 (t, J=8.34 Hz, 1 H) 7.71 (d, J=1.77 Hz, 2 H) 8.21 (s, 1 H) 8.40 (d, J=7.83 Hz, 1 H) 8.50 (s, 2 H). [M+H] calc'd for C32H42F2N8O4, 641; found 641.

Provenance & Evidence