HCID 178489496, compound → HCID 178489497, compound

HRID 2289716Notes

Reaction equation

HRID 2289716 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([O:12][C:13](=[O:43])[CH2:14][N:15]([S:25]([C:28]1[CH:37]=[C:36]2[C:31]([C:32]([Cl:42])=[CH:33][N:34]=[C:35]2[NH:38][C:39]([NH2:41])=[NH:40])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])(C)(C)C>C(C(O)=O)(F)(F)F.C1(C)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:42][C:32]1[C:31]2[C:36](=[CH:37][C:28]([S:25]([N:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:14][C:13]([OH:43])=[O:12])(=[O:26])=[O:27])=[CH:29][CH:30]=2)[C:35]([NH:38][C:39]([NH2:41])=[NH:40])=[N:34][CH:33]=1

Participants

4

Reactant 1

HCID 178489496HCID 178489496, compound

Product 1

HCID 178489497HCID 178489497, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(2-methoxybenzyl)glycine t-butyl ester trifluoroacetate (150 mg, 0.231 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, azeotroping with PhMe, and the residue triturated with i-Pr2O to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(2-methoxybenzyl)glycine trifluoroacetate (122 mg, 0.206 mmol) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroping with PhMe
  3. customthe residue triturated with i-Pr2O

Sources & evidence

ORD record
ord-e3e65aa237254adb93841f0244d38d96
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

Loading…