Water → HCID 68183027, compound

Participants

Reaction Steps

A mixture of methyl 5-allyl-4-(3,4-dichlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylate (0.118 g, 0.245 mmol), methanol (2.0 mL), tetrahydrofuran (2.0 mL) and a solution of 1.0 M sodium hydroxide in water (1.50 mL, 1.50 mmol) was stirred at rt overnight. Additional methanol (2.0 mL) and 1.0 M Sodium hydroxide in water (1.50 mL, 1.50 mmol) was added. The mixture was stirred at rt for 2 days. The mixture was concentrated to remove most of volatile solvents and then acidified by 1M HCl. The precipitate was collected and dried in air to afford crude product. Final purification by HPLC afforded pure product as a white solid (43.3 mg, 23%). LCMS (FA) ES+: 467, 469. 1H NMR (400 MHz, DMSO) δ 7.45 (d, J=8.3 Hz, 1H), 7.38 (s, 1H), 7.25 (br s, 1H), 7.12 (d, J=8.2 Hz, 1H), 6.50 (s, 1H), 6.04 (s, 1H), 5.74-5.63 (m, 1H), 4.99-4.89 (m, 2H), 4.18 (s, 1H), 3.68 (br s, 4H), 3.12 (br s, 4H), 2.54-2.50 (m, 2H, overlapping with DMSO peak).

Provenance & Evidence