Hydrochloric Acid → HCID 178429422, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethylamino)-4-(5-(4-fluorophenylsulfonyl)thiophen-2-yl)pyrimidin-5-yl)benzonitrile (110 mg, 0.19 mmol), trimethylsilyl azide (178 mg, 1.52 mmol) and dibutyltin oxide (47 mg, 0.19 mmol) in N,N-dimethylformamide (5 mL) was heated at 120° C. for 24 h. After cooling to rt, 10 mL of aqueous hydrochloric acid (10%) was added and the resulting mixture was stirred for 30 min. Saturated sodium bicarbonate was added to adjust to pH 5 and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the product purified by flash chromatography eluting with methanol (containing 10% acetic acid)/dichloromethane (1:20). MS (M+H)+ 634.

Provenance & Evidence