Ammonium Chloride → HCID 76284627, compound

Participants

Reaction Steps

3-[5-(2-Chloro-benzyloxy)-pyridin-2-yl]-isoxazole-5-carboxylic acid (which may be prepared as described in Preparation of Intermediate 10; 220 mg, 0.67 mmol), NH4Cl (71 mg, 1.33 mmol), N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (258 mg, 1.33 mmol), and 1-hydroxybenzotriazole (183 mg, 1.33 mmol) were taken up in THF (8 mL). Diisopropylethylamine (235 μL, 1.33 mmol) was added and the mixture was stirred overnight under nitrogen. The solvent was evaporated and the residue was purified by flash chromatography on silica, eluting with 50% EtOAc/hexanes, to give 3-[5-(2-chloro-benzyloxy)-pyridin-2-yl]-isoxazole-5-carboxylic acid amide (117.5 mg, 53%) as off-white flakes. HRMS Calcd. for C16H13ClN3O3 (M+H)+, 330.0640. Found: 330.0638.

Provenance & Evidence