Acetone → {4-[6-[2-(4-Cyano-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-butyl}-trimethyl-ammonium formate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{5-[2-(4-dimethylamino-butylamino)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-pyrazol-1-yl}-benzonitrile (Ex. 30, 44 mg, 0.079 mmol) in acetone (0.4 mL) was added methylbenzenesulfonate (12 μL, 0.087 mmol) at ambient temperature. The reaction mixture was heated at 55° C. under N2 for 2.5 hrs. A further quantity of methylbenzenesulfonate (3.2 μL) was added and the mixture was heated at 55° C. for 1 hr. Once cooled the volatiles were evaporated in vacuo and the residue azeotroped with diethyl ether. The resultant residue was subjected to preparative C18 HPLC, eluting with a gradient of 20-70% MeCN in water (+0.1% formic acid) to give the title compound as a white solid (10 mg).

Provenance & Evidence