Ammonium Chloride → HCID 15908562, compound

Participants

Reaction Steps

A solution of N2-(4-methoxybenzoyl)-2,3-pyridinediamine (92 mg, 0.38 mmol) in tetrahydrofuran (1 mL) was treated with potassium hexamethyldisilazide (160 mg, 0.80 mmol). After 0.25 hr, the mixture was treated with 4-tert-butylbenzoyl chloride. After 0.75 hr, the mixture was poured into a mixture of aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed twice with water, once with saturated sodium chloride solution, dried (magnesium sulfate), and filtered. Concentration in vacuo and purification of the residue by flash cromatography (silica gel, methylene chloride/ethyl acetate) followed by recrystallization from ethyl acetate/hexanes yielded 31 mg (20%) of the title compound.

Provenance & Evidence