Water → HCID 68707270, compound

Participants

Reaction Steps

Methyl 3-(6-(3-(1-acetyl-4-methylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)propanoate (125 mg, 0.230 mmol) was dissolved in THF (10 mL) and potassium tert-butoxide (64.6 mg, 0.576 mmol) was added. The reaction was stirred for 30 seconds and 2-bromoethyl acetate (38.5 mg, 0.230 mmol) was added. The reaction was stirred for 3 hours. Water was added and the reaction was extracted with dichloromethane. The organic layer was concentrated, and the crude material was purified by silica gel chromatography (5-7% methanol in dichloromethane) to give 2-(6-(3-(1-acetyl-4-methylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)ethyl acetate (89 mg, 0.164 mmol, 71.2% yield).

Provenance & Evidence