Guanidine Hydrochloride → HCID 178461817, compound

HRID 2289732Notes

Reaction equation

Cl.[CH2:2]([N:9]([S:15]([C:18]1[CH:27]=[C:26]2[C:21]([C:22]([Cl:32])=[CH:23][N:24]=[C:25]2[NH:28][C:29]([NH2:31])=[NH:30])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:10]([C:12]([OH:14])=[O:13])[CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.NC(N)=N.[C:38](OC(=O)[C@H](C)N(CC1C=CC=CC=1)S(C1C=C2C(C(Cl)=CN=C2Cl)=CC=1)(=O)=O)([CH3:41])([CH3:40])[CH3:39]>COCCOC>[C:38]([O:13][C:12](=[O:14])[C@H:10]([CH3:11])[N:9]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[S:15]([C:18]1[CH:27]=[C:26]2[C:21]([C:22]([Cl:32])=[CH:23][N:24]=[C:25]2[NH:28][C:29]([NH2:31])=[NH:30])=[CH:20][CH:19]=1)(=[O:17])=[O:16])([CH3:41])([CH3:40])[CH3:39]

Participants

Conditions

Temperature: 60 °C

Procedure

N-Benzyl-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-alanine hydrochloride ##STR30## NaH (30 mg, 80% dispersion by wt in mineral oil, 1.01 mmol) was added in one portion to a stirred suspension of guanidine hydrochloride (154 mg, 1.61 mmol) in DME (5.0 mL) and the mixture was heated at 60° C. under N2 for 45 min. A solution of N-benzyl-N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-L-alanine t-butyl ester (200 mg, 0.40 mmol) in DME (2.0 mL) was added and the mixture heated at 95° C. for 4 h. The solvents were evaporated in vacuo and the residue was purified by column chromatography upon silica gel using pentane-EtOAc (50:50 to 20:80) as eluant to give N-benzyl-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-alanine t-butyl ester (120 mg, 0.225 mmol) as pale yellow foam after repeated evaporation from CH2Cl2,

Workup

temperaturethe mixture heated at 95° C. for 4 h
customThe solvents were evaporated in vacuo
customthe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record: ord-01b28ddb19e040029181da06076672ae
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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