Ethanolamine → 3-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isothiazole-5-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 1920939Notes

Reaction equation

HRID 1920939 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][C:21]([F:24])=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].[CH2:25]([CH2:27][NH2:28])[OH:26]>>[CH:13]([NH2:14])([CH3:18])[CH3:12].[OH:26][CH2:25][CH2:27][NH:28][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][C:21]([F:24])=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 674922713-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isothiazole-5-carboxylic acid methyl ester

Product 2

HCID 6363IsopropylamineHCID 468973573-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isothiazole-5-carboxylic acid (2-hydroxy-ethyl)-amideYield 141.5%

Procedure

As described for example 38b, 3-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isothiazole-5-carboxylic acid methyl ester (120 mg, 0.34 mmol), was converted, using ethanolamine (25 mg, 0.41 mmol), instead of isopropyl amine, to the title compound (91 mg, 70%) which was obtained as a white solid after purification by chromatography (silica, dichloromethane:methanol=97.5:2.5 to 9:1). MS: m/e=379.3 [M+H]+.

Sources & evidence

ORD record
ord-8628b06608a5438584709a8d22af3f8d
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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