Methyl iodide → Cgp-20712

HRID 638062Notes

Reaction equation

HRID 638062 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][C:39]=1[OH:40])[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:36])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[NH:28][CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:31]=2)=[CH:23][CH:22]=1)(=[O:9])[NH2:8].CI>CN(C)C=O>[C:7]([C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][C:39]=1[OH:40])[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:36])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]([CH3:1])[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:31]=2)=[CH:25][CH:26]=1)(=[O:9])[NH2:8].[C:7]([C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][C:39]=1[OH:40])[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([OH:36])[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:31]([CH3:1])[C:30]([C:32]([F:35])([F:34])[F:33])=[CH:29][N:28]=2)=[CH:25][CH:26]=1)(=[O:9])[NH2:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178513694HCID 178513694, compound

Product 2

HCID 2685Cgp-20712HCID 202551541-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.48 g of potassium tert.-butoxide is added while stirring in an ice bath to a solution of 1 g of the 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[4-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol obtained according to Example 3 in 20 ml of dimethylformamide. After 10 minutes, a solution of 0.3 g of methyl iodide in 1 ml of dimethylformamide is added dropwise over a period of 20 minutes. The mixture is then stirred for 2 hours at room temperature, the solvent is removed in a rotary evaporator and the residue is chromatographed on silica gel with a solvent mixture of chloroform/methanol/ammonia (700:50:1), yielding the two isomeric compounds 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° and 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)-1H-imidazol-2-yl]-phenoxy]-2-propanol having a melting point of 157°-159°.

Workup

  1. customobtained
  2. customthe solvent is removed in a rotary evaporator
  3. customthe residue is chromatographed on silica gel with a solvent mixture of chloroform/methanol/ammonia (700:50:1)

Sources & evidence

ORD record
ord-cae42ef60d0b4c64be3d8aa4dae3865b
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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