(3S)-oxolan-3-amine hydrochloride → (s)-2-[(e)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid (tetra-hydro-furan-3-yl)-amide

HRID 1923562Notes

Reaction equation

HRID 1923562 reaction equation
C(O[C:4]([C:6]1[S:10][C:9](/[CH:11]=[CH: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.Cl.[O:26]1[CH2:30][CH2:29][C@H:28]([NH2:31])[CH2:27]1>>[O:26]1[CH2:30][CH2:29][C@H:28]([NH:31][C:4]([C:6]2[S:10][C:9](/[CH:11]=[CH: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]1

Participants

3

Reactant 2

HCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 66643683HCID 66643683, compound

Product 1

HCID 131729716(s)-2-[(e)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid (tetra-hydro-furan-3-yl)-amideYield 89%

Procedure

As described for example 63b, 2-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid ethyl ester (50 mg, 0.15 mmol) was converted, using (S)-tetrahydrofuran-3-amine HCl instead of 4-aminotetrahydropyran, to the title compound (50 mg, 89%) which was obtained as a white solid. MS: m/e=382.3 [M+H]+.

Sources & evidence

ORD record
ord-983a67e109694fd49438ead22866d13b
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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