Dimethylformamide dimethyl acetal → HCID 178474390, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-acetylamino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid amide (Int. 22, 100 mg, 0.27 mmol) in THF (2 mL) was added N,N-dimethylformamide dimethyl acetal, (53 μL, 0.40 mmol) and the reaction mixture was heated at 100° C. for 10 mins using microwave irradiation. The solvent was removed in vacuo to afford crude 2-acetylamino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid 1-dimethylamino-meth-(E)-ylideneamide intermediate. To a solution of the material thus obtained in acetic acid (2 mL) was added 4-hydrazino-benzonitrile hydrochloride (43 mg, 0.25 mmol). The mixture was heated at 90° C. for 15 minutes using microwave irradiation. The solvent was removed in vacuo and the residue azeotroped with toluene (2×5 mL). The resultant residue was purified by flash chromatography eluting with a gradient of 0-100% cyclohexane in EtOAc and then with 10% MeOH in EtOAc followed by preparative C18 HPLC, eluting with a gradient of 10-90% MeCN in water (+0.1% formic acid) to afford the title compound as a white solid (15 mg).

Provenance & Evidence