5-[2-(Benzylamino)-ethoxy]-salicylamide → 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol

HRID 638050Notes

Reaction equation

HRID 638050 reaction equation
[O:1]1[CH2:21][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:20])[C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][N:15]=2)=[CH:7][CH:6]=1.[CH2:22]([NH:29][CH2:30][CH2:31][O:32][C:33]1[CH:41]=[C:37]([C:38]([NH2:40])=[O:39])[C:36]([OH:42])=[CH:35][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[CH2:22]([N:29]([CH2:30][CH2:31][O:32][C:33]1[CH:34]=[CH:35][C:36]([OH:42])=[C:37]([C:38](=[O:39])[NH2:40])[CH:41]=1)[CH2:21][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]([CH3:20])[C:13]([C:16]([F:17])([F:19])[F:18])=[CH:14][N:15]=2)=[CH:9][CH:10]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 137544195-[2-(Benzylamino)-ethoxy]-salicylamideHCID 202551182-[4-(2,3-epoxypropoxy)-phenyl]-1-methyl-5-(trifluoromethyl)-1H-imidazole

Product 1

HCID 202550861-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5 g of the resulting 2-[4-(2,3-epoxypropoxy)-phenyl]-1-methyl-5-(trifluoromethyl)-1H-imidazole and 4.7 g of 5-[2-(benzylamino)-ethoxy]-salicylamide in 100 ml of isopropanol is heated under reflux for 15 hours and the solvent is subsequently removed in a rotary evaporator. The crude 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol obtained in the form of an oil is further processed in that form.

Workup

  1. temperatureunder reflux for 15 hours
  2. customthe solvent is subsequently removed in a rotary evaporator

Sources & evidence

ORD record
ord-8c472a81dfd14561b50107a6cb7a16c5
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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