Dimethylformamide → HCID 67316036, compound

Participants

Reaction Steps

A slurry of 2-({2-chloro-5-fluoro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid (0.68 g, 1.420 mmol) in THF (100 mL) was treated with a drop of DMF, followed by a solution of oxalyl chloride (2M in CH2Cl2, 2.84 mL, 5.48 mmol). After 30 min Et20 (50 mL) was added. The resulting slurry was filtered and the solids were washed with Et2O, then dried in vacuum to obtain 5-chloro-1,8-difluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride as a pale yellow solid (580 mg, 82%). 1H NMR (400 MHz, THF-d8) δ ppm 2.41 (s, 3H), 7.14 (dd, J=10.07, 8.61 Hz, 1H), 7.45 (d, 8.06 Hz, 3H), 7.56 (d, J=2.56 Hz, 1H), 7.69-7.83 (m, 1H), 8.09 (d, J=8.42 Hz, 2H), 10.84 (br s, 1H); ESIMS (M+H)+=460.98.

Provenance & Evidence