HCID 178491118, compound → HCID 178491121, compound

HRID 2289722Notes

Reaction equation

HRID 2289722 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]([S:18]([C:21]1[CH:30]=[C:29]2[C:24]([C:25]([Cl:35])=[CH:26][N:27]=[C:28]2[NH:31][C:32]([NH2:34])=[NH:33])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(C)(C)C>C(C(O)=O)(F)(F)F.C1(C)C=CC=CC=1>[Cl:35][C:25]1[C:24]2[C:29](=[CH:30][C:21]([S:18]([N:8]([CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[CH2:7][C:6]([OH:36])=[O:5])(=[O:19])=[O:20])=[CH:22][CH:23]=2)[C:28]([NH:31][C:32]([NH2:34])=[NH:33])=[N:27][CH:26]=1

Participants

4

Reactant 1

HCID 178491118HCID 178491118, compound

Product 1

HCID 178491121HCID 178491121, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(4-methoxybenzyl)glycine t-butyl ester (65 mg, 0.122 mmol) was dissolved in CF3CO2H (1.0 mL) and the mixture stirred at room temperature for 40 min. The mixture was diluted with PhMe, concentrated in vacuo, and the residue purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880NH3 (83:15:3) as eluant to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(4-methoxybenzyl)glycine (11 mg, 0.023 mmol) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-f2a5cc7aa5c544ed93cb51ef29cd687a
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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