Hydrochloric Acid → HCID 67393178, compound

Participants

Reaction Steps

To a mixture of 1,1-dimethylethyl 4-[4-[[methyl[(1R)-1-phenylethyl]amino]carbonyl]-2-thiazolyl]-1-piperidinecarboxylate (2.0 g, 4.65 mmol) (see PCT Patent Publication WO 2007/014290 for a method of preparation) in diethyl ether was added hydrochloric acid (2 N in diethyl ether, 23 mL). The reaction mixture was stirred at room temperature for 3 h, and then the solid was collected by filtration to give N-methyl-N-[(1R)-1-phenylethyl]-2-(4-piperidinyl)-4-thiazolecarboxamide hydrochloride (1.2 g). A mixture of N-methyl-N-[(1R)-1-phenylethyl]-2-(4-piperidinyl)-4-thiazolecarboxamide hydrochloride (0.11 g, 0.30 mmol), (2-[(2,2,2-trifluoroethylidene)amino]oxy]acetic acid (prepared by the method described Example 1, Step E) (62 mg, 0.36 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (81 mg, 0.42 mmol), N-hydroxybenzotriazole (5 mg) and triethylamine (0.10 mL, 0.72 mmol) in dry methylene chloride (8 mL) was stirred at room temperature for 3 h. The reaction mixture was diluted with methylene chloride and then washed with water, hydrochloric acid (0.1 N), water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound, a compound of the present invention, as a thick oil (130 mg).

Provenance & Evidence