3-Thiophenamine, tetrahydro-, 1,1-dioxide → N-(1,1-Dioxo-tetrahydro-thiophen-3-yl)-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinamide

HRID 332413Notes

Reaction equation

HRID 332413 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.[O:24]=[S:25]1(=[O:31])[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26]1>>[O:24]=[S:25]1(=[O:31])[CH2:29][CH2:28][CH:27]([NH:30][C:19](=[O:21])[C:18]2[CH:22]=[CH:23][C:15]([O:14][CH2:13][C:3]3[C:4]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[N:5][O:6][C:2]=3[CH3:1])=[N:16][CH:17]=2)[CH2:26]1

Participants

3

Reactant 2

HCID 228073-Thiophenamine, tetrahydro-, 1,1-dioxideHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 68937579N-(1,1-Dioxo-tetrahydro-thiophen-3-yl)-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinamideYield 54%

Procedure

As described for example 8b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.65 mmol) was converted, using 1,1-dioxo-tetrahydro-thiophen-3-ylamine instead of methylamine, to the title compound (150 mg, 54%) which was obtained as a white solid. MS: m/e=428.2 [M+H]+.

Sources & evidence

ORD record
ord-df72d94fd2994d92b59c93f3a6656d70
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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