Hydrochloric Acid → HCID 67439985, compound

Participants

Reaction Steps

To a suspension of 3-(6-(methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid (100 mg, 0.30 mmol.) in dichloromethane (6.7 mL) was added N-hydroxybenzotriazole (59.7 mg, 0.44 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.hydrochloric acid (169.7 mg, 0.44 mmol.), followed by 4-methylmorpholine (89.5 mg, 0.89 mmol) and the resultant mixture was stirred at room temperature for 1 h. Then 2-methoxyethanamine (26.6 mg, 0.44 mmol) was added to the flask and the reaction mixture was stirred under nitrogen overnight. Thin layer chromatography (petroleum ether:ethyl acetate=1:1) and LC-MS showed the reaction was complete. The reaction was quenched with water and extracted with dichloromethane (twice). The combined organic layers were washed with 2% sodium hydroxide aqueous solution (twice) and water (3 times), dried over anhydrous sodium sulfate. Removal of the solvent in vacuo gave 130 mg of crude product as a yellow oil, which was dissolved in methanol (3 mL) and treated with sodium borohydride (20 mg, 0.53 mmol) for an additional 3 h. LC-MS showed the reaction was complete. The reaction was quenched with water and extracted with ethyl acetate, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford crude product, which was further purified by column chromatography (petroleum ether:ethyl acetate=1:1) from methanol to give 100 mg of methyl 2-(3-(2-methoxy ethylcarbamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a white crystal. Yield: 85.6%.

Provenance & Evidence