Hydrochloric Acid → 6-cyclopropyl-5-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

4-(5-amino-2-cyclopropylpyridin-3-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one (21 mg, 0.058 mmol) was suspended in a mixture of water (1 mL) and con. HCl (1 mL), cooled suspension to 0° C., a solution of sodium nitrite (4 mg, 0.058 mmol) in water was added slowly. After 5 mins, the reaction mixture was neutralised by the addition of NaHCO3 solution. Then the resultant suspension was added in aliquots to a solution of copper (I) cyanide (5 mg, 0.058 mmol) and sodium cyanide (6 mg, 0.11 mmol) in water at room temperature. Heated to 70° C. for 30 mins. Extracted with EtOAc, evaporated organic solvent, the residue was purified with Prep HPLC. (0-100% CH3CN/H2O) to afford 1.2 mg of 6-cyclopropyl-5-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)nicotinonitrile.

Provenance & Evidence