Oxolan-3-amine → 3-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amide

HRID 1920942Notes

Reaction equation

HRID 1920942 reaction equation
CO[C:3]([C:5]1[S:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].COC(C1ON=C([O:31][CH2:32][C:33]2[C:34]([C:39]3C=CC=CN=3)=[N:35]OC=2C)C=1)=O.NC1CCOC1>>[CH:13]([NH2:14])([CH3:18])[CH3:12].[O:31]1[CH2:32][CH2:33][CH:34]([NH:35][C:3]([C:5]2[S:9][N:8]=[C:7]([O:10][CH2:11][C:12]3[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=3[CH3:17])[CH:6]=2)=[O:4])[CH2:39]1

Participants

5

Reactant 3

HCID 3365553Oxolan-3-amineHCID 674920483-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl esterHCID 674921853-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester

Product 2

HCID 6363IsopropylamineHCID 594481363-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amideYield 16%

Procedure

As described for example 14e, 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester (165 mg, 0.53 mmol), instead of 3-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester, was converted, using 3-aminotetrahydrofuran (56 mg, 0.64 mmol), instead of isopropyl amine, to the title compound (32 mg, 16%) which was obtained as a colourless gum after purification by chromatography (silica, heptane:ethyl acetate=4:1 to 0:1). MS: m/e=366.2 [M+H]+.

Sources & evidence

ORD record
ord-16b48af1d60a438e8c26e21bc2c75b97
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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