Sodium hydride → HCID 178498287, compound

HRID 2289700Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=3[O:26][CH3:27])[C:20]([OH:22])=[O:21])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[C:6]([NH:28][C:29]([NH2:31])=[NH:30])=[N:5][CH:4]=1.[H-].[Na+].Cl[C:35]1C2C(=CC=C(S(NC3C=C(C=CC=3OC)C(OC)=O)(=O)=O)C=2)C(Cl)=CN=1>CS(C)=O>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([NH:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=3[O:26][CH3:27])[C:20]([O:22][CH3:35])=[O:21])(=[O:14])=[O:15])=[CH:10][CH:11]=2)[C:6]([NH:28][C:29]([NH2:31])=[NH:30])=[N:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-{[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}-4-methoxybenzoic acid hydrochloride ##STR12## Guanidine hydrochloride (179.8 mg, 1.88 mmol) was added in one portion to a suspension of NaH (54.9 mg, 80% dispersion by wt in mineral oil, 1.83 mmol) in DMSO (10 mL) and the mixture was heated at 60° C. under N2 for 20 min. Methyl 3-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-4-methoxybenzoate (238.6 mg, 0.541 mmol) was added and the mixture heated at 90° C. for 24 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 to 90:10:1) as eluant to give methyl 3-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}-4-methoxybenzoate (203.2 mg, 0.43 mmol) as a pale yellow solid.

Workup

temperaturethe mixture heated at 90° C. for 24 h
customThe solvents were evaporated in vacuo
customthe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record: ord-97157b394df04e27beb1c05237c16607
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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