3-Thiophenamine, tetrahydro-, 1,1-dioxide → HCID 49781589, compound

HRID 1923631Notes

Reaction equation

HRID 1923631 reaction equation
[CH2:1]([C:5]1[C:9](/[CH:10]=[CH:11]/[C:12]2[S:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[O:22]=[S:23]1(=[O:29])[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24]1>>[O:22]=[S:23]1(=[O:29])[CH2:27][CH2:26][CH:25]([NH:28][C:18]([C:14]2[S:13][C:12](/[CH:11]=[CH:10]/[C:9]3[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=3[CH3:21])=[N:16][C:15]=2[CH3:17])=[O:20])[CH2:24]1

Participants

3

Reactant 2

HCID 228073-Thiophenamine, tetrahydro-, 1,1-dioxideHCID 595685392-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 49781589HCID 49781589, compoundYield 82%

Procedure

As described for example 104, 2-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid (153 mg, 0.5 mmol) was converted, using 1,1-dioxidotetrahydrothien-3-ylamine instead of rac-2-amino-1-butanol, to the title compound (174 mg, 82%) which was obtained as a white solid after purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) and recrystallization from ethyl acetate/heptane. MS: m/e=424.2 [M+H]+.

Sources & evidence

ORD record
ord-393352c491364f06b3bb9c1b5fc42d77
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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