Ethanolamine → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 1920933Notes

Reaction equation

CO[C:3]([C:5]1[S:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].[CH2:24]([CH2:26][NH2:27])[OH:25]>>[CH:13]([NH2:14])([CH3:18])[CH3:12].[OH:25][CH2:24][CH2:26][NH:27][C:3]([C:5]1[S:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4]

Participants

Reactant 2

HCID 700Ethanolamine

HCID 674921363-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester

Product 2

HCID 6363Isopropylamine

HCID 468972633-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid (2-hydroxy-ethyl)-amideYield 111.3%

Procedure

As described for example 34, 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester (100 mg, 0.3 mmol), was converted, using ethanolamine (21 mg, 0.34 mmol), instead of isopropyl amine, to the title compound (60 mg, 58%) which was obtained as a white solid after purification by chromatography (silica, dichloromethane:methanol=1:0 to 9:1). MS: m/e=360.1 [M+H]+.

Sources & evidence

ORD record: ord-4ac02fb632714b3094cf2d27ca898bbb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173652B2

Reaction notes

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