Isoniazid → 4-(5-{2-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]propyl}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

Oxalylchloride (2M in DCM, 0.28 mL, 0.55 mmol) was dropwise added during 5 minutes to a solution of 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]-N-methylbutanamide (140 mg, 0.5 mmol) and 2,6-lutidine (0.12 mL, 1 mmol) in DCM (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and isonicotinic acid hydrazide (103 mg, 0.75 mmol) was added. DCM was evaporated after 4 h stirring at r.t. Sat. aq. NaHCO3 (10 mL) was added to the residue and the mixture was refluxed for 16 h. The reaction was allowed to attain r.t., followed by extracted with CHCl3 (3×20 mL). The combined organic phases were dried (MgSO4), concentrated and purified by prep HPLC to yield the title compound (3 mg, 2%).

Provenance & Evidence