Acetic Acid → HCID 70976697, compound

Participants

Reaction Steps

A solution of ethyl 6-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (for a preparation see Intermediate 27)(240 mg, 0.557 mmol) in ethanol (5 mL) was treated with aqueous lithium hydroxide (1N, 1.115 mL, 1.115 mmol) and the resulting mixture was stirred at room temperature. After 1 h most of the ethanol was removed in vacuo, the residue was diluted with water (ca 2 mL) and the “cloudy” mixture was treated with acetic acid (0.064 mL, 1.115 mmol). The precipitate formed was isolated by filtration, washed with Et2O and dried at 60° C. for 16 h to give 6-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)nicotin ic acid (150 mg, 0.373 mmol, 66.9% yield) as a pale yellow solid which was used in the next step without further purification. LCMS (HpH, 2 min), Rt=0.61 min, MH+=403.

Provenance & Evidence