2486-69-3 → 4-(9-Cyclopentyl-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

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Reaction Steps

2-Chloro-9-cyclopentyl-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 1.50-2.01 (m, 8 H) 3.32 (s, 3 H) 3.89 (s, 3 H) 4.04 (t, J=14.15 Hz, 2 H) 4.75 (q, 1 H) 7.50 (d, J=8.34 Hz, 1 H) 7.52 (s, 1 H) 7.90 (s, 1 H) 8.19 (d, J=8.34 Hz, 1 H) 8.25 (s, 1 H). [M+H] calc'd for C21H23F2N5O4, 447; found 447.

Provenance & Evidence