Dimethylformamide → HCID 118235501, compound

Participants

Reaction Steps

The sodium salt of Example 44 (200 mg, 0.378 mmol) was suspended in dichloromethane (25 mL). A drop of DMF was added, followed by oxalyl chloride (50 mg, 0.39 mmol). The mixture was stirred at room temperature for 2 h, then 2-(morpholin-4-yl)ethanol (99 mg, 0.75 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed with aqueous sodium bicarbonate solution and the organic layer was concentrated in vacuo. Chromatography (silica, 0 to 10% MeOH in DCM), followed by freeze-drying, gave the title compound (35 mg, 15%) as an off-white solid. δH (DMSO-d6) 8.64 (s, 2H), 8.37 (s, 1H), 7.55-7.43 (m, 2H), 7.31-7.10 (m, 4H), 7.04-7.01 (m, 1H), 4.35 (s, 2H), 4.34-4.28 (m, 2H), 4.25-4.21 (m, 2H), 3.52-3.48 (m, 4H), 3.36-3.25 (m, 2H), 2.60-2.54 (m, 2H), 2.42-2.38 (m, 4H), 2.32 (s, 3H), 2.10-2.04 (m, 2H), 1.45-1.35 (m, 2H), 1.19 (s, 3H). LCMS (pH10): MH+ (621.8), RT 2.01 minutes.

Provenance & Evidence