5-Fluoro-o-toluidine → HCID 57955524, 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), 5-fluoro-2-methylaniline (60 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, 39%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40-1.96 (m, 9 H) 2.22 (s, 3 H) 3.99 (t, J=14 Hz, 2 H) 4.62 (t, J=8 Hz, 1 H) 6.81 (td, J=8, 3 Hz, 1 H) 7.19 (t, J=8 Hz, 1 H) 7.58 (dd, J=12, 3 Hz, 1 H) 8.20 (s, 1 H) 8.57 (s, 1 H). [M+H] calc'd for C20H22F3N5O, 406; found 406.

Provenance & Evidence