5-(2-Bromoethoxy)salicylamide → Cgp-20712

HRID 638045Notes

Reaction equation

HRID 638045 reaction equation
[NH2:1][CH2:2][CH:3]([OH:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]([CH3:21])[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=2)=[CH:8][CH:7]=1.Br[CH2:24][CH2:25][O:26][C:27]1[CH:35]=[C:31]([C:32]([NH2:34])=[O:33])[C:30]([OH:36])=[CH:29][CH:28]=1>>[C:32]([C:31]1[CH:35]=[C:27]([CH:28]=[CH:29][C:30]=1[OH:36])[O:26][CH2:25][CH2:24][NH:1][CH2:2][CH:3]([OH:22])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]([CH3:21])[CH:14]=[C:15]([C:17]([F:20])([F:18])[F:19])[N:16]=2)=[CH:10][CH:11]=1)(=[O:33])[NH2:34]

Participants

3

Reactant 2

HCID 137544205-(2-Bromoethoxy)salicylamideHCID 202551961-amino-3-[4-(1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl)-phenoxy]-2-propanol

Product 1

HCID 2685Cgp-20712

Procedure

A mixture of 1.5 g of 1-amino-3-[4-(1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl)-phenoxy]-2-propanol and 0.82 g of 5-(2-bromoethoxy)-salicylamide is stirred for 1 hour in an oil bath at a temperature of 100°. The melt is then extracted by boiling with 30 ml of isopropanol. The filtered solution is concentrated to 15 ml, cooled and the crystals that are precipitated are filtered off. Recrystallisation from methanol yields 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(1-methyl-4-(trifluoromethyl)-1H-imidazol-2-yl)-phenoxy]-2-propanol having a melting point of 195°-197°.

Workup

  1. extractionThe melt is then extracted
  2. concentrationThe filtered solution is concentrated to 15 ml
  3. temperaturecooled
  4. customthe crystals that are precipitated
  5. filtrationare filtered off
  6. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-6b30949cae6f45b78386ba4048b8c0ef
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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