4-Aminotetrahydropyran → 4-(9-cyclohexyl-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-(tetrahydro-2H-pyran-4-yl)benzamide

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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 tetrahydro-2H-pyran-4-amine. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.43 (m, 3 H) 1.49-1.90 (m, 11 H) 3.19-3.32 (m, 3 H) 3.32-3.46 (m, 2 H) 3.84-3.92 (m, 2 H) 3.94 (d, J=9.0 Hz, 3 H) 3.97-4.08 (m, 1 H) 4.07-4.23 (m, 2 H) 4.38-4.58 (m, 1 H) 7.42-7.61 (m, 2 H) 8.06-8.17 (m, 1 H) 8.24 (br. s., 2 H) 8.62 (br. s., 1 H). [M+H] calc'd for C27H34F2N6O4 545; found 545.

Provenance & Evidence