Methylamine → HCID 68319533, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.17 mL, 1.99 mmol) in anhydrous THF (20 mL) is added methylamine 2.0M in THF (0.99 mL, 1.99 mmol) at 0° C. The solution is stirred at 0° C. to room temperature for 0.5 hours and added to a stirred solution of 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-N-hydroxy-benzamidine (350 mg, 0.9 mmol) in anhydrous pyridine (5 mL). The reaction mixture is stirred at room temperature for 1 hour and then heated to 50° C. and stirred for 16 hours. The reaction mixture is cooled to room temperature and concentrated in vacuo. Dichloromethane is added and the organics washed sequentially with saturated NaHCO3 (20 mL) solution and H2O (20 mL) then dried (Na2SO4), filtered and concentrated. Purification via flash chromatography (25 g silica gel, 50-60% EtOAc/heptane) affords 3-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-[1,2,4]oxadiazole-5-carboxylic acid methylamide (150 mg, 37%)

Provenance & Evidence