4-Methylmorpholine → HCID 11965207, compound

Participants

Reaction Steps

To a stirring solution of 6-(4-trifluoromethoxy-phenylsulfanyl)-nicotinic acid sodium salt (54 mg, 0.158 mmol) (see Intermediate 8) and n-methyl morpholine (0.02 mL, 0.158 mmol) in dichloromethane (2.0 mL) in a 0° C. ice bath, add 2-chloro-4,6-dimethoxy-1,3,5-triazine (28 mg, 0.158 mmol). Remove the ice bath and stir for 45 minutes. After this time, add (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (24 mg, 0.158 mmol) and stir at room temperature for 2 hours. After this time, wash the reaction with saturated aqueous sodium bicarbonate while extracting with 10% isopropanol/dichloromethane. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Purify via chromatography eluting with 2M ammonia in methanol and dichloromethane. Dissolve the purified free base in minimal dichloromethane and add 1M HCl in ether in slight excess followed by hexane. Concentrate in vacuo to give the titled compound. MS (m/e): 452.2 (M+1).

Provenance & Evidence