Water → HCID 178512657, compound

Participants

Reaction Conditions

Reaction Steps

NaH (13.6 mg, 80% dispersion by wt in mineral oil, 0.45 mmol) was added in one portion to a solution of guanidine hydrochloride (44 mg, 0.46 mmol) in DMSO (2 mL) and the mixture was heated at 80° C. under N2 for 10 min. 1,4-Dichloro-7-(phenylsulfanyl)isoquinoline (60 mg, 0.195 mmol) was added and the mixture heated at 80° C. for 1 h. The cooled mixture was poured into water (20 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was extracted with hexanes-i-Pr2O and this organic solution was decanted, and then stirred with a solution of HCl in Et2O to give a precipitate. The white solid was collected by filtration and dried in vacuo to give 4-chloro-1-guanidino-7-(phenylsulphanyl)isoquinoline (51 mg, 0.13 mmol).

Provenance & Evidence