Sodium Chloride → HCID 136365312, compound

A mixture of ethyl 3,4,5,6-tetrahydro-6-hydroxy-1-H-cyclohepta[cd]indole-2-carboxylate (0.30 g, 1.16 mmol), sodium methoxide (1.26 g, 23.1 mmol), guanidine hydrochloride (2.22 g, 23.1 mmol) and N,N-dimethylformamide (15 ml) was stirred at room temperature for 3 days. The reaction mixture was poured into a 5% aqueous sodium chloride solution, followed by extraction with ethyl acetate (three times). The extract solution was washed twice with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain crude N-(aminoiminomethyl)-3,4,5,6-tetrahydro-6-hydroxy-1H-cyclohepta [cd]indole-2carboxamide. This crude product was added to a solution of methanesulfonic acid (0.22 g) in tetrahydrofuran (12 ml) and the resulting mixture was stirred at 0°-5° C. The insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. A 5% aqueous sodium chloride solution was added to the thus obtained residue, and the resulting mixture was made basic with 28% aqueous ammonia and extracted twice with ethyl acetate. The extract solution was washed with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=96/4) to obtain N-(aminoiminomethyl)-3,4-dihydro-1H-cyclohepta[cd]indole-2-carboxamide (0.16 g). This compound (0.16 g) was treated with a solution of methanesulfonic acid (0.15 g) in tetrahydrofuran (3.5 ml) to obtain N-(aminoiminomethyl)-3,4-dihydro-1H-cyclohepta[cd]indole-2-carboxamide methanesulfonate (0.11 g).

1. extractionfollowed by extraction with ethyl acetate (three times)
2. washThe extract solution was washed twice with a 5% aqueous sodium chloride solution
3. dry with materialdried over anhydrous magnesium sulfate
4. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-bae9c0f1f36744168e488003ddc17753

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05814654