4-(Bromomethyl)benzonitrile → 1-[2-(4-Cyanobenzyloxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole

HRID 543788Notes

Reaction equation

HRID 543788 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:17])=[N:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:5]1.[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)#[N:19]>CO>[F:15][C:13]([F:14])([F:16])[CH2:12][N:11]=[C:10]([NH2:17])[NH:9][C:6]1[CH:7]=[CH:8][N:4]([CH2:3][CH2:2][O:1][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([C:18]#[N:19])=[CH:21][CH:22]=2)[N:5]=1

Participants

4

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 212798481-(2-Hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole

Product 1

HCID 202028101-[2-(4-Cyanobenzyloxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazoleYield 19.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2-hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (2.51 g.) and p-cyanobenzyl bromide (1.96 g.) was heated at 140° for 10 minutes. The melt, on cooling, was dissolved in MeOH (5 ml.) and purified by chromatography on silica gel using EtOAc/EtOH/triethylamine 9:1:1 v/v/v as eluant to give 4-(2-[3-(2-[2,2,2-trifluoroethyl]guanidino)pyrazol-1-yl]ethoxymethyl)benzonitrile (700 mg.; 19%).

Workup

  1. temperaturewas heated at 140° for 10 minutes
  2. temperatureThe melt, on cooling
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-e42922cb9258460b8f5a013f5ee683f1
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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