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

HRID 544564Notes

Reaction equation

HRID 544564 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>[C:18]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:1][CH2:2][CH2:3][N:4]2[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:17])=[N:11][CH2:12][C:13]([F:14])([F:16])[F:15])=[N:5]2)=[CH:22][CH:21]=1)#[N:19]

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 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2-hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (2.5 g.) and 4-cyanobenzyl bromide (1.96 g.) was heated at 140° for 10 minutes. When cool, the residue was dissolved in a little MeOH and purified by medium pressure chromatography on silica gel using triethylamine/EtOH/EtOAc 1:10:95 v/v/v as eluant to give 1-[2-(4-cyanobenzyloxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (yield 55%) having the following n.m.r. spectrum in d6DMSO: 7.5 (br m, 5H); 5.85 (d, 1H); 5.1 (s, 2H); 4.05 (br m, 4H); 3.7 (br t, 2H).

Workup

  1. temperaturewas heated at 140° for 10 minutes
  2. temperatureWhen cool
  3. custompurified by medium pressure chromatography on silica gel

Sources & evidence

ORD record
ord-421a52cdad7e467f9a85a7e37fef0676
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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