Oxolan-3-amine → 2-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amide

HRID 1923609Notes

Reaction equation

HRID 1923609 reaction equation
CO[C:3]([C:5]1[S:9][C:8](/[CH:10]=[CH:11]/[C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:7][C:6]=1[CH3:22])=[O:4].[NH2:23][CH:24]1[CH2:28][CH2:27][O:26][CH2:25]1>>[O:26]1[CH2:27][CH2:28][CH:24]([NH:23][C:3]([C:5]2[S:9][C:8](/[CH:10]=[CH:11]/[C:12]3[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=3[CH3:17])=[N:7][C:6]=2[CH3:22])=[O:4])[CH2:25]1

Participants

3

Reactant 2

HCID 3365553Oxolan-3-amineHCID 666436512-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 497811502-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amideYield 46%

Procedure

As described for example 93d, 2-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid methyl ester (80 mg, 0.25 mmol) was converted, using 3-amino-tetrahydrofuran instead of isopropylamine, to the title compound (43 mg, 46%) which was obtained as a white solid. MS: m/e=376.3 [M+H]+.

Sources & evidence

ORD record
ord-4dd4b47caf1741bcb18fa3c66ada270d
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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