HCID 178461817, compound → HCID 178461820, compound

HRID 2289733Notes

Reaction equation

HRID 2289733 reaction equation
C([O:5][C:6](=[O:35])[C@H:7]([CH3:34])[N:8]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[S:9]([C:12]1[CH:21]=[C:20]2[C:15]([C:16]([Cl:26])=[CH:17][N:18]=[C:19]2[NH:22][C:23]([NH2:25])=[NH:24])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(C)(C)C>CCOC(C)=O.Cl>[ClH:26].[CH2:27]([N:8]([S:9]([C:12]1[CH:21]=[C:20]2[C:15]([C:16]([Cl:26])=[CH:17][N:18]=[C:19]2[NH:22][C:23]([NH2:25])=[NH:24])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C@H:7]([C:6]([OH:35])=[O:5])[CH3:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 178461817HCID 178461817, compound

Product 1

HCID 178461820HCID 178461820, compoundYield 157.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyl-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-alanine t-butyl ester (100 mg, 0.19 mmol) was dissolved in a solution of EtOAc saturated with HCl (5.0 mL) and the mixture stirred at room temperature for 18 h. The mixture was concentrated in vacuo, azeotroping with EtOAc, to give N-benzyl-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-alanine hydrochloride (77 mg, 0.15 mmol) as a white powder.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customazeotroping with EtOAc

Sources & evidence

ORD record
ord-17f14fbb6b40428193cabbcdd39ddf3b
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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