Trifluoroacetic acid → 4-(2-(pyridin-4-yl)pyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)quinazoline-7-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2,4-dimethoxybenzyl)-4-oxo-N-(1,2,4-thiadiazol-5-yl)-3,4-dihydroquinazoline-7-sulfonamide (0.611 g, 1.330 mmol) and BOP (0.765 g, 1.729 mmol) in acetonitrile (6.65 ml) was added DBU (0.301 ml, 1.995 mmol). The reaction was stirred for 10 minutes at 40° C. 4-(pyrrolidin-2-yl)pyridine (0.272 ml, 1.995 mmol) was added and the reaction was stirred for 8 hours at 40° C. 4-(pyrrolidin-2-yl)pyridine (0.272 ml, 1.995 mmol) was added and the reaction was stirred for four hours at 40° C. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40 g, gradient elution 0-10% MeOH:DCM). The material was dissolved in DCM and TFA (0.2 ml, 2.60 mmol) was added. The reaction was stirred for one hour at room temperature. The reaction was concentrated and purified via column chromatography (RediSep Gold 12 g, gradient elution 0-10% MeOH:DCM) to afford 4-(2-(pyridin-4-yl)pyrrolidin-1-yl)-N-(1,2,4-thiadiazol-5-yl)quinazoline-7-sulfonamide as a light yellow solid. (ESI) 440.2 (M+H)+.

Provenance & Evidence