3-Fluoroaniline → HCID 57955605, compound

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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 (100 mg, 0.32 mmol), 3-fluoroaniline (54 mg, 0.48 mmol), i-PrOH (2 mL) and conc. HCl (5 drops) were heated to 100° C. overnight to give the title compound. The final compound was purified by reverse phase HPLC and basified to give the free base (50 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58-1.96 (m, 8H) 4.04 (t, J=14 Hz, 2H) 4.78 (m, 1H) 6.59-6.87 (m, 1H) 7.16-7.33 (m, 1H) 7.38 (d, J=8 Hz, 1H) 7.79 (d, J=12 Hz, 1H) 8.26 (s, 1H) 9.66 (br. s., 1H). [M+H] calc'd for C19H20F3N5O, 392. found 392.

Provenance & Evidence