Water → Ammonia

Participants

Reaction Conditions

Reaction Steps

N"-{4-Chloro-7-[(10-oxo-9-oxa-6-azaspiro [4.5]dec-6-yl)sulphonyl]-1-isoquinolinyl}guanidine hydrochloride ##STR98## NaH (45 mg, 80% dispersion in mineral oil, 1.5 mmol) was added to a solution of guanidine hydrochloride (231 mg, 2.4 mmol) in DMSO (5 ml), and the solution stirred at 50° C. for 20 min. Ethyl 1-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl][2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}cyclopentanecarboxylate (330 mg, 0.6 mmol) was added and the reaction stirred at 70° C. for 21/2 h. The cooled reaction was poured into water, extracted with EtOAc, and the combined organic extracts washed with brine, dried (MgSO4) and evaporated in vacuo. The residual yellow gum was purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880 NH3 (95:5:0.5) as eluant to give ethyl 1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl][2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}cyclopentanecarboxylate as an orange oil.

Provenance & Evidence