Triethylamine → 3-(3-(2-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methyl-N-(1-methyl-1H-pyrazol-5-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzoic acid (2.44 g, 6.7 mmol) and thionyl chloride (30 ml, 411 mmol, Aldrich) was heated to 95° C. for 2 h. The volatiles were removed in vacuo. The solids were re-dissolved in CH2Cl2 (30 ml). A 10 ml aliquot of this solution (860 mg, 2.2 mmol) was treated with 1-methyl-1H-pyrazol-5-amine (656 mg, 6.7 mmol, Maybridge), followed by triethylamine (939 μl, 6.7 mmol, Aldrich). The mixture was diluted with 10% Na2CO3 and extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4, filtered and concentrated over silica gel. The residue was purified using column chromatography (Acetone/Hexanes=0-50%). The mixture was dissolved in MeOH and loaded onto an Agilent AccuBOND II SCX solid phase extraction column. After washing with MeOH, the title compound was eluted with 2M NH3 in MeOH. The residue was recrystallized from MeOH yielding the title compound as a white solid. HRMS (TOF) Calcd for C24H20ClN6O+: 443.1382, found: 443.1389.

Provenance & Evidence