1,1'-Carbonyldiimidazole → HCID 58476281, compound

Participants

Reaction Steps

A solution of 3-(6-(methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid (330 mg, 0.88 mmol) and 1,1′-carbonyldiimidazole (500 mg, 3.08 mmol) in tetrahydrofuran (6 mL) was heated to 60° C. for 2 h, then was cooled to room temperature and treated with pyrazin-2-amine (92.2 mg, 0.97 mmol,). After stirring for 20 min, the reaction mixture was treated with dropwise addition of a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (670 mg, 4.4 mmol) in tetrahydrofuran (2 mL). Upon completion of addition, the resultant mixture was stirred overnight. Thin layer chromatography (dichloromethane:ethyl acetate=5:1) showed the reaction was nearly complete. The reaction mixture was quenched with brine and acidified with 1N hydrochloric acid solution to pH=6, extracted with ethyl acetate (twice). The combined organic layers were washed with brine for 3 times, dried over anhydrous magnesium sulfate. Removal of the solvent in vacuo gave crude product, which was purified by column chromatography (dichloromethane:ethyl acetate=5:1) to afford 175 mg of methyl 3,3-dimethyl-2-(3-(pyrazin-2-ylcarbamoyl)-phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as a white solid. Yield: 47.5%. MS (ESI+APCI) M+1=417.2.

Provenance & Evidence