Triethylamine → HCID 66796056, compound

Participants

Reaction Steps

A solution of 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid (140 mg, 0.61 mmol) (i.e. the product of Example 13, Step E) in dichloromethane (2 mL) and a catalytic amount of N,N-dimethylformamide (1 drop) was treated with oxalyl chloride (0.1 mL, 1.1 mmol) and stirred at ambient temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure and re-dissolved in dichloromethane (1 mL). The reaction mixture was added to a stirred suspension of N-methyl-2-(4-piperidinyl)-N-[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]-4-thiazolecarboxamide monohydrochloride (i.e. the product of Example 6, Step C) (280 mg, 0.72 mmol), triethylamine (0.2 mL, 1.5 mmol), and potassium carbonate (300 mg, 2.1 mmol) in dichloromethane (2 mL). The reaction mixture was then heated to reflux for 4 h, and then cooled to ambient temperature. The resulting suspension was diluted with dichloromethane (10 mL), filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography using 50-100% ethyl acetate in hexanes as eluant to give 130 mg of the title product, a compound of the present invention as an oil.

Provenance & Evidence