Oxalyl chloride → HCID 25150091, compound

Participants

Reaction Steps

A mixture of 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoic acid (28 g, 63.2 mmol) in THF (500 mL) was treated with 2 drops of DMF and oxalyl chloride (8.30 mL, 95 mmol), and was stirred at rt for 3 h. The resulting slurry was filtered to obtain 5-chloro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrogen chloride as a yellow solid (27.67 g, 95%). 1H NMR (free base) (400 MHz, DMSO-d6) δ ppm 2.37 (s, 3H), 7.07 (d, 4.21 Hz, 1H), 7.34 (d, J=4.21 Hz, 1H), 7.47 (d, 8.06 Hz, 2H), 7.53-7.63 (m, 1H), 7.78-7.90 (m, 1H), 8.00 (d, J=8.42 Hz, 2H), 8.18 (dd, J=7.78 Hz, 1.74 Hz, 1H), 9.28 (d, J=8.42 Hz, 1H); ESIMS (M+H)+=424.97.

Provenance & Evidence