Hydrogen Peroxide → 4-(2-[3-(2-[2,2,2-Trifluoroethyl]guanidino)pyrazol-1-yl]ethoxymethyl)benzamide

HRID 543785Notes

Reaction equation

HRID 543785 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]=[C:5]([NH2:24])[NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:8]=1.[OH:27]O.[OH-].[Na+]>CO>[F:26][C:2]([F:1])([F:25])[CH2:3][N:4]=[C:5]([NH2:24])[NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]([NH2:21])=[O:27])=[CH:18][CH:17]=2)[N:8]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 202028101-[2-(4-Cyanobenzyloxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole

Product 1

HCID 202027974-(2-[3-(2-[2,2,2-Trifluoroethyl]guanidino)pyrazol-1-yl]ethoxymethyl)benzamideYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2-[3-(2-[2,2,2-trifluoroethyl]guanidino)pyrazol-1-yl]ethoxymethyl)benzonitrile (650 mg.) in MeOH (5 ml.) was added hydrogen peroxide (30%, 100 volume) (2 ml.) followed by N aqueous NaOH (1 ml.). The mixture was then stirred at room temperature for 2.25 hours. The solvent was then evaporated in vacuo to give a yellow gum (700 mg.). This gum was purified by medium pressure chromatography using EtOAc/EtOH/triethylamine 96:3:1 v/v/v as eluant to give 4-(2-[3-(2-[2,2,2-trifluoroethyl]guanidino)pyrazol-1-yl]ethoxymethyl)benzamide (210 mg.; 31%) having the following n.m.r. in d6DMSO: 7.5 (m, 4H); 7.5 (d, 1H); 5.8 (d, 1H); 5.0 (s, 2H); 4.0 (m, 4H); 3.7 (m, 2H).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customto give a yellow gum (700 mg.)
  3. customThis gum was purified by medium pressure chromatography

Sources & evidence

ORD record
ord-937f77c7043a4316b15b0ba4f9d625c0
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

Loading…