Oxolan-3-amine → 3-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isothiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amide

HRID 1920940Notes

Reaction equation

HRID 1920940 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].[NH2:25][CH:26]1[CH2:30][CH2:29][O:28][CH2:27]1>>[CH:13]([NH2:14])([CH3:18])[CH3:12].[O:28]1[CH2:29][CH2:30][CH:26]([NH:25][C:3]([C:5]2[S:9][N:8]=[C:7]([O:10][CH2:11][C:12]3[C:13]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=4)=[N:14][O:15][C:16]=3[CH3:17])[CH:6]=2)=[O:4])[CH2:27]1

Participants

4

Reactant 2

HCID 3365553Oxolan-3-amineHCID 674922713-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isothiazole-5-carboxylic acid methyl ester

Product 2

HCID 6363IsopropylamineHCID 468973583-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isothiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amideYield 55.3%

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 3-aminotetrahydrofuran (36 mg, 0.41 mmol), instead of isopropyl amine, to the title compound (38 mg, 27%) which was obtained as a white solid after purification by chromatography (silica, heptane:ethyl acetate=75:25 to 25:75). MS: m/e=405.3 [M+H]+.

Sources & evidence

ORD record
ord-22d56900ad9a4a9ab39d73a1cb77c8fa
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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