4-Amino-1-Boc-piperidine → (R)-4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-vinyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-N-(1-(2-(dimethylamino)acetyl)piperidin-4-yl)-3-methoxybenzamide

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 N,N-dimethylacetyl chloride. The title product using preparative HPLC and neutralized with bicarbonate. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.41-2.05 (m, 12 H) 2.19 (s, 6 H) 2.92-3.21 (m, 4 H) 3.28 (s, 3 H) 3.72-3.87 (m, 2 H) 3.94 (s, 3 H) 3.99-4.20 (m, 2 H) 4.36 (d, J=15.41 Hz, 1 H) 4.89 (d, J=8.34 Hz, 1 H) 5.31-5.45 (m, 2 H) 6.01 (ddd, J=17.49, 12.69, 10.74 Hz, 1 H) 7.47 (d, J=1.77 Hz, 2 H) 7.83 (s, 1 H) 8.15 (d, J=7.83 Hz, 2 H) 8.31 (d, J=8.08 Hz, 1 H). [M+H] calc'd for C32H43FN8O4, 623; found 623.

Provenance & Evidence