Sodium hydride → HCID 178451120, compound

HRID 2289704Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:21])=[O:20])=[CH:16][CH:17]=2)[C:12]([NH:28][C:29]([NH2:31])=[NH:30])=[N:11][CH:10]=1.[H-].[Na+].[C:34](OC(=O)CCNS(C1C=C2C(C(Cl)=CN=C2Cl)=CC=1)(=O)=O)([CH3:37])([CH3:36])[CH3:35]>COCCOC.CCOC(C)=O>[C:34]([O:26][C:25](=[O:27])[CH2:24][CH2:23][NH:22][S:19]([C:15]1[CH:14]=[C:13]2[C:18]([C:9]([Cl:8])=[CH:10][N:11]=[C:12]2[NH:28][C:29]([NH2:31])=[NH:30])=[CH:17][CH:16]=1)(=[O:20])=[O:21])([CH3:37])([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 30 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-β-alanine trifluoroacetate ##STR14## Guanidine hydrochloride (140 mg, 1.46 mmol was added in one portion to a stirred suspension of NaH (35 mg, 80% dispersion by wt in mineral oil, 1.17 mmol) in DME (8.0 mL) and the mixture was heated at 30° C. under N2 for 30 min. N-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-β-alanine t-butyl ester (150 mg, 0.37 mmol) was added and the mixture heated at 90° C. for 18 h. The cooled mixture was diluted with EtOAc, washed with water, brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880NH3 (97:3:0.3 to 95:5:0.5) as eluant to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-β-alanine t-butyl ester (75 mg, 0.175 mmol) as a yellow foam

Workup

temperaturethe mixture heated at 90° C. for 18 h
washwashed with water, brine
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record: ord-b165a4e7a33a485db37504232297708d
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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