Ammonia → N-(aminoiminomethyl)-5,6-dihydro-6-isopropoxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

Crude N-(aminoiminomethyl)-5,6-dihydro-6-hydroxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide was obtained by carrying out reaction according to the method described in Example 1, except for using ethyl 5,6-dihydro-6-hydroxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate (0.70 g, 2.70 mmol), guanidine hydrochloride (2.58 g, 27.0 mmol), sodium methoxide (1.46 g, 27.0 mmol) and N,N-dimethylformamide (40 ml). This compound was dissolved in a solution of methanesulfonic acid (1.0 g) in isopropanol (50 ml) and the resulting solution was stirred at 60° C. for 30 minutes. Subsequently, the reaction solution was poured into ice water, made basic with 28% aqueous ammonia and then extracted three times with ethyl acetate. The extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=97/3) to obtain 0.37 g of N-(aminoiminomethyl)-5,6-dihydro-6-isopropoxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide. This compound was treated with methanesulfonic acid (0.29 g) in a mixed solvent of tetrahydrofuran and diethyl ether to obtain N-(aminoiminomethyl)-5,6-dihydro-6-isopropoxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide methanesulfonate.

Provenance & Evidence