HCID 54689915, compound → HCID 54689860, compound

Participants

Reaction Conditions

Reaction Steps

The 3-(4-benzyloxy-3,5-dichloro-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (125 mg, 0.281 mmol) was dissolved in 30% HBr/AcOH (1.3 mL) and sealed in a reaction tube with stirring for 40 minutes at 70° C. The reaction is cooled to room temperature and concentrated in vacuo. The resulting solid is washed with Et2O and filtered, then placed under high vacuum for 2 hours. The solid is taken up in NH4OH (2 mL) and stirred at room temperature for 1 hour. The reaction mix is concentrated and taken up in 1M HCl. The resulting solid is filtered and rinsed with water to give 66 mg of a white solid (0.18 mmol, 66% yield). 1H NMR (300 MHz, DMSO-D6) δ 12.45 (bs, 1H), 10.18 (bs, 1H), 7.42 (s, 2H), 7.08 (s, 1H), 4.60 (bs, 1H). MS (ESI APCI) positive ion 353 (M+H)+; negative ion 351 (M−H)−.

Provenance & Evidence