Acetyl chloride → HCID 178473989, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, succinic anhydride (105 mg, 1.05 mmol) and triethylamine (279 μl, 2.00 mmol) were added to a solution of the cis-4-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine hydrochloride (282 mg, 1.00 mmol) obtained in Example 410 in toluene (6 ml) at room temperature, and the resulting mixture was refluxed. After 5.5 hours, the reaction solution was poured into water and extracted with ethyl acetate. The extract solution was concentrated under reduced pressure, and to a solution of the resulting residue in ethyl acetate (4 ml) was added acetyl chloride (214 μl, 3.00 mmol), and the resulting mixture was heated to 100° C. Dimethylformamide (2 ml) was added thereto because a solid was precipitated. After 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The extract solution was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain cis-1-{4-[(1-acetyl-4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}pyrrolidine-2,5-dione (123.7 mg, 33%).

Provenance & Evidence