Water → HCID 178512653, compound

Participants

Reaction Conditions

Reaction Steps

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-aspartic acid trifluoroacetate ##STR71## NaH (53 mg, 80% dispersion in mineral oil, 1.77 mmol) was added to a solution of guanidine hydrochloride (168 mg, 1.76 mmol) in DMSO (6 mL) and the solution ws heated to 50° C. for 30 min. N-[(1,4-Dichloro-7-isoquinolinyl)carbonyl]-DL-aspartic acid a,,-di-t-butyl ester (330 mg, 0.70 mmol) was added and the mixture heated at 80-90° C. overnight. The cooled mixture was poured into water (50 mL) and extracted with EtOAc extract (5×20 mL). The combined organic extracts were washed with water, brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by (i), trituration with i-Pr2O (ii), column chromatography on silica gel using CH2Cl2 -MeOH-0.880NH3 (95:5:0.5) as eluant, and (iii), crystallisation from i-Pr2O, to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-aspartic acid at,-di-t-butyl ester (145 mg, 0.29 mmol) as a yellow solid.

Provenance & Evidence