2-Amino-2-methyl-1-propanol → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 1923644Notes

Reaction equation

HRID 1923644 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]([O:11][CH2:12][C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][O:16][C:17]=2[CH3:18])=[N:8][CH:7]=1)=[O:5])C.[NH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28]>>[OH:28][CH2:27][C:26]([NH:25][C:4]([C:6]1[S:10][C:9]([O:11][CH2:12][C:13]2[C:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:15][O:16][C:17]=2[CH3:18])=[N:8][CH:7]=1)=[O:5])([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 595684942-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 497809272-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideYield 23%

Procedure

As described for example 127, 2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester (95 mg, 0.28 mmol) was converted, using 2-amino-2-methyl-1-propanol instead of isopropylamine, to the title compound (25 mg, 23%) which was obtained as a colourless gum after purification by chromatography (silica, 0 to 3% methanol in dichloromethane). MS: m/e=388.3 [M+H]+.

Sources & evidence

ORD record
ord-fdf97fc8d8c2415180aa582e16b5b000
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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