HCID 178470425, compound → HCID 178518629, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-(4-chloro-2-aminobenzoyl)-3-trifluoromethyl-1H-pyrazole-5-carboxylate (360 mg, 0.997 mmol) in toluene (50 mL) was added 2-hydroxypyridine (93.9 mg, 0.988 mmol). Toluene was removed by distillation and the residue was heated at 170° C. for 2 days. The flask was cooled to room temperature and dichloromethane (20 mL) was added. The insoluble material was filtered to give crude solid (284 mg). The crude material was continuously chromatographed eluting with dichloromethane (100 mL) and dichloromethane:2-propanol (98:2, 200 mL). The fractions were concentrated by rotary evaporation and were found to contain a contaminant from tygon tubing. The fractions were combined and flash chromatographed through a plug of silica gel to remove the contaminant, eluting with hexanes, hexanes:ethyl acetate (95:5, 90:10), dichloromethane, and dichloromethane:2-propanol (95:5, 90:10). The product fractions were concentrated by rotary evaporation to give the title compound as a white solid (124 mg, 37%, m.p. 337-339° C.).

Provenance & Evidence