Sodium hydride → HCID 178484747, compound

HRID 2289706Notes

Reaction equation

FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([S:26]([N:29]([CH3:34])[CH2:30][C:31]([OH:33])=[O:32])(=[O:28])=[O:27])=[CH:23][CH:24]=2)[C:19]([NH:35][C:36]([NH2:38])=[NH:37])=[N:18][CH:17]=1.[H-].[Na+].[C:41](OC(=O)CN(S(C1C=C2C(C(Cl)=CN=C2Cl)=CC=1)(=O)=O)C)([CH3:44])([CH3:43])[CH3:42]>COCCOC>[C:41]([O:32][C:31](=[O:33])[CH2:30][N:29]([S:26]([C:22]1[CH:21]=[C:20]2[C:25]([C:16]([Cl:15])=[CH:17][N:18]=[C:19]2[NH:35][C:36]([NH2:38])=[NH:37])=[CH:24][CH:23]=1)(=[O:27])=[O:28])[CH3:34])([CH3:44])([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 50 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-methylglycine bis(trifluoroacetate) ##STR15## Guanidine hydrochloride (286 mg, 2.99 mmol was added in one portion to a stirred suspension of NaH (77.5 mg, 80% dispersion by wt in mineral oil, 2.58 mmol) in DME (2.0 mL) and the mixture was heated at 50° C. under N2 for 20 min. A solution of N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-methylglycine t-butyl ester (393 mg, 0.97 mmol) in DME (10 mL) was added and the mixture heated at 90° C. for 2 h. The solvents were evaporated in vacuo and the residue was purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880NH3 (97:3:0.3) as eluant to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-methylglycine t-butyl ester (260 mg, 0.607 mmol) as an off-white foam

Workup

temperaturethe mixture heated at 90° C. for 2 h
customThe solvents were evaporated in vacuo
customthe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record: ord-10767beda11141b78f43f3266ea8673c
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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