4-Amino-1-Boc-piperidine → HCID 57955556, compound

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Reaction Steps

Using the general procedure for amide bond synthesis, 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)-2-fluoro-5-methoxybenzoic acid was first reacted with tert-butyl 4-aminopiperidine-1-carboxylate. The product was diluted to ethyl acetate, washed by sodium bicarbonate aqueous solution and brine. Organic extract was dried and concentrated to a residue. It was then dissolved in a mixture of TFA and MeOH (1:1) and stirred for 1 h. After which, it was concentrated in vacuo, separated between ethyl acetate and sodium bicarbonate aqueous solution. Organic extract dried and concentrated to a residue, which was subjected to amide bond synthesis with 2-(dimethylamino)acetic acid. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (m, 2 H) 1.61 (m, 4 H) 1.73 (br. s., 4 H) 1.99 (s, 3 H) 2.19 (s, 6 H) 2.73 (m, 1 H) 3.14 (m, 3 H) 3.80-3.95 (m, 3 H) 3.95-4.20 (m, 4 H) 4.26 (m., 1 H) 4.81 (d, J=8.1 Hz, 1 H) 7.19 (d, J=6.8 Hz, 1 H) 7.92-8.10 (m, 2 H) 8.18-8.35 (m, 2 H). [M+H] calc'd for C30H39F3N8O4, 633; found 633.

Provenance & Evidence