Dimethyl Sulfoxide → HCID 86693782, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (1.22 mL, 14.1 mmol) in dichloromethane (15 mL) at −60° C. is added dropwise a solution of dimethyl sulfoxide (2.08 mL, 29.3 mmol) in dichloromethane (15 mL) and stirred at −60° C. for 15 min. trans-2-chloro-4-[(3-hydroxytetrahydropyran-4-yl)amino]-3-methyl-benzonitrile (3.13 g, 11.7 mmol, Example 9) in dichloromethane (30 mL) is added to the solution and stirred at −60° C. for 30 min. Triethylamine (9 mL, 64.5 mmol) is added and the mixture is warmed to room temperature and stirred for 3 h. The mixture is diluted with EtOAc and washed twice with 1 N hydrochloric acid. The organic portion is dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude title compound as an orange semi-solid (2.53 g, 81%). LC-ES/MS m/z 265.2 (M+1).

Provenance & Evidence