4-Aminotetrahydropyran → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 1923641Notes

Reaction equation

HRID 1923641 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][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[O:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:4]([C:6]2[S:10][C:9]([O:11][CH2:12][C:13]3[C:14]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[N:15][O:16][C:17]=3[CH3:18])=[N:8][CH:7]=2)=[O:5])[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 595684942-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 497809242-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amideYield 56%

Procedure

As described for example 127, 2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester (100 mg, 0.28 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (65 mg, 56%) which was obtained as a white solid after purification by chromatography (silica, 0 to 3% methanol in dichloromethane). MS: m/e=398.0 [M+H]+.

Sources & evidence

ORD record
ord-ce070bbf8c7449db963e28b66f5058e2
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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