1-Phenylcyclohexylamine → N-(1-phenylcyclohexyl)-1H-indazole-5-carboxamide

Beteiligte Stoffe

Reaktionsschritte

Oxalyl dichloride (38.7 μl, 0.444 mmol) and N,N-dimethylformamide (about 1 μl) were added to a solution of the 1H-indazole-5-carboxylic acid (40.0 mg, 0.247 mmol) obtained in Reference Example 1 in dichloromethane (2.5 ml), and the resulting mixture was stirred at room temperature for 0.5 hour and then was stirred with heating under reflux for 2 hours while maintaining the temperature. The reaction solution was concentrated to dryness and a solution of the resulting residue in tetrahydrofuran (1.5 ml) was added dropwise to a solution of 1-phenylcyclohexylamine (130 mg, 0.742 mmol) in tetrahydrofuran (2.0 ml). The resulting mixture was stirred for 18 hours while being maintained at room temperature. A 5% aqueous sodium bicarbonate solution was added to the reaction solution and stirred, followed by extraction with ethyl acetate. The organic phase was washed with a 5% aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The organic phase dried was concentrated under reduced pressure, and the resulting crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol=50/1 to 30/1) to obtain N-(1-phenylcyclohexyl)-1H-indazole-5-carboxamide (62 mg, 78%).

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