HCID 178451175, compound → HCID 178479400, compound

HRID 2289743Notes

Reaction equation

HRID 2289743 reaction equation
C([O:5][C:6](=[O:30])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:24]=[C:23]2[C:18]([C:19]([Cl:29])=[CH:20][N:21]=[C:22]2[NH:25][C:26]([NH2:28])=[NH:27])=[CH:17][CH:16]=1)(=[O:14])=[O:13])(C)(C)C>CCOC(C)=O.Cl>[ClH:29].[Cl:29][C:19]1[C:18]2[C:23](=[CH:24][C:15]([S:12]([N:8]3[CH2:9][CH2:10][CH2:11][C@H:7]3[C:6]([OH:30])=[O:5])(=[O:14])=[O:13])=[CH:16][CH:17]=2)[C:22]([NH:25][C:26]([NH2:28])=[NH:27])=[N:21][CH:20]=1

Participants

4

Reactant 1

HCID 178451175HCID 178451175, compound

Product 1

HCID 178479400HCID 178479400, compoundYield 146.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-proline t-butyl ester (60 mg, 0.13 mmol) was dissolved in a solution of EtOAc saturated with HCl (5.0 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo , azeotroping with EtOAc, and the residue triturated with CH2Cl2 to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-proline hydrochloride (44 mg, 0.095 mmol) as a white powder.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customazeotroping with EtOAc
  3. customthe residue triturated with CH2Cl2

Sources & evidence

ORD record
ord-0802880f7a9b4929b271060288a8b8bf
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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