Ethanolamine → 2-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 1923638Notes

Reaction equation

HRID 1923638 reaction equation
CO[C:3]([C:5]1[S:9][C:8]([CH2:10][CH:11]([C:13]2[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:15][O:16][C:17]=2[CH3:18])O)=[N:7][CH:6]=1)=[O:4].[CH2:23]([CH2:25][NH2:26])[OH:24]>>[OH:24][CH2:23][CH2:25][NH:26][C:3]([C:5]1[S:9][C:8](/[CH:10]=[CH:11]/[C:13]2[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:15][O:16][C:17]=2[CH3:18])=[N:7][CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 666436782-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-2-hydroxy-ethyl]-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 497818062-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid (2-hydroxy-ethyl)-amideYield 35%

Procedure

As described for example 124b, 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-2-hydroxy-ethyl]-thiazole-5-carboxylic acid methyl ester (90 mg, 0.29 mmol) was converted, using ethanolamine instead of isopropylamine, to the title compound (35 mg, 35%) which was obtained as a light yellow solid after purification by chromatography (silica, 0 to 10% methanol in dichloromethane). MS: m/e=336.3 [M+H]+.

Sources & evidence

ORD record
ord-08d746e493a64628bc10fa6553b3b605
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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