Guanidine Hydrochloride → HCID 178451317, compound

Participants

Reaction Conditions

Reaction Steps

N-[(-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]glycine trifluoroacetate ##STR13## NaH (29 mg, 80% dispersion by wt in mineral oil, 0.97 mmol) was added in one portion to a stirred solution of guanidine hydrochloride (146 mg, 1.52 mmol) in DMSO (2.0 mL) and the mixture was heated at 60° C. under N2 for 30 min. N-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]glycine t-butyl ester (150 mg, 0.38 mmol) was added and the mixture heated at 90° C. for 9 h. The cooled mixture was diluted with water (30 mL), extracted with EtOAc (4×20 mL) and the combined organic extracts were washed with water, brine, dried (Na2SO4) and evaporated in vacuo. The residue was dissolved in Et2O and a solution of HCl in Et2O (1 M) was added to give a sticky precipitate. The Et2O was decanted and the residue triturated with EtOAc to give a white solid. Filtration with EtOAc and Et2O washing gave N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]glycine t-butyl ester hydrochloride (68 mg, 0.14 mmol).

Provenance & Evidence