HCID 178461680, compound → HCID 178461682, compound

HRID 2289731Notes

Reaction equation

HRID 2289731 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]([S:17]([C:20]1[CH:29]=[C:28]2[C:23]([C:24]([Cl:34])=[CH:25][N:26]=[C:27]2[NH:30][C:31]([NH2:33])=[NH:32])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])(C)(C)C>CCOC(C)=O.Cl>[ClH:34].[Cl:34][C:24]1[C:23]2[C:28](=[CH:29][C:20]([S:17]([N:8]([C@H:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH3:10])[CH2:7][C:6]([OH:35])=[O:5])(=[O:18])=[O:19])=[CH:21][CH:22]=2)[C:27]([NH:30][C:31]([NH2:33])=[NH:32])=[N:26][CH:25]=1

Participants

4

Reactant 1

HCID 178461680HCID 178461680, compound

Product 1

HCID 178461682HCID 178461682, compoundYield 147.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-[(1S)-1-phenylethyl]glycine t-butyl ester (100 mg, 0.19 mmol) was dissolved in a solution of EtOAc saturated with HCl (4.0 mL) and the mixture stirred at room temperature for 4 h. The mixture was concentrated in vacuo and the residue triturated with EtOAc to give N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-[(1S)-1-phenylethyl]glycine hydrochloride (72 mg, 0.14 mmol) as a white powder.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue triturated with EtOAc

Sources & evidence

ORD record
ord-522a538710824dcda379591aa78332d4
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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