2486-69-3 → 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-benzoic acid

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Reaction Steps

2-Chloro-9-cyclohexyl-7,7-difluoro-5-methyl-8,9-dihydro-5H-pyrimido[5,4-b][1,4]diazepin-6(7H)-one (2.77 g, 8.8 mmol), 4-amino-3-methoxy benzoic acid (1.61 g, 9.6 mmol), i-PrOH (30 mL) and conc. HCl (30 drops) were heated to 95° C. for 18 hours. A this time the reaction was cooled to room temperature and filtered to reveal the product as a tan solid (2.74 g, 70% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21 (d, J=12.13 Hz, 1 H) 1.23-1.42 (m, 2 H) 1.53-1.78 (m, 5 H) 1.82 (d, J=12.63 Hz, 2 H) 3.32 (s, 3 H) 3.94 (s, 3 H) 4.26 (t, J=12.38 Hz, 2 H) 4.52 (t, J=11.62 Hz, 1 H) 7.47-7.65 (m, 2 H) 8.13 (d, J=8.08 Hz, 1 H) 8.28-8.45 (m, 1 H) 9.43 (br. s., 1 H). [M+H] calc'd for C22H25F2N5O4, 462; found 462.

Provenance & Evidence