Guanidine Hydrochloride → HCID 178430100, compound

Participants

Reaction Conditions

Reaction Steps

1.37 g (25.37 mmol) of sodium methoxide are added at a temperature in the region of 20° C. under an argon atmosphere to 25 mL of methanol. After complete dissolution, 2.5 g (26.2 mmol) of guanidine hydrochloride are added. After stirring at a temperature in the region of 20° C. for 1 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is suspended in 25 mL of 1,2-dimethoxyethane and then again concentrated to dryness. The residue is suspended in a mixture of 50 mL of tetrahydrofuran, 25 mL of acetonitrile and 50 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere and then 1.18 g (4.36 mmol) of 3-chlorocarbonyl-1-(isoquinol-1-yl)-4-methyl-1H-pyrrole, dissolved in 20 mL of chloroform, are added thereto. After stirring at a temperature in the region of 20° C. for 18 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is triturated in 100 mL of water. After filtering, a gum is obtained, which gum is dissolved in 50 mL of methanol. The solution obtained is partially concentrated to a volume of 5 to 10 mL and is then purified by silica gel chromatography [eluent: chloroform/methanol (75/25 by volume)]. After concentrating the fractions under reduced pressure and triturating in ethyl ether, 0.62 g of 3-guanidinocarbonyl-1-(isoquinol-1-yl)-4-methyl-1H-pyrrole hydrochloride is obtained in the form of a white solid melting at 247° C. Mass spectrum (EI): EI: m/e 293 (M+.), m/e 234.

Provenance & Evidence