5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → N-(3-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1685787Notes

Reaction equation

HRID 1685787 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][C:8]=1[CH3:15])[CH2:4][CH3:5])[CH3:2].[OH:16][CH2:17][C:18]([NH:20][CH2:21][C@H:22]([OH:36])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[NH:34])[NH:32]O)=[C:27]([CH3:35])[CH:26]=1)=[O:19]>>[CH2:4]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:14][N:34]=[C:31]([C:28]3[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH:22]([OH:36])[CH2:21][NH:20][C:18](=[O:19])[CH2:17][OH:16])=[CH:26][C:27]=3[CH3:35])[N:32]=2)=[CH:9][C:8]=1[CH3:15])[CH2:1][CH3:2])[CH3:5]

Participants

3

Reactant 2

HCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178429065HCID 178429065, compound

Product 1

HCID 42639463N-(3-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 5.2%

Procedure

The title compound (3 mg) is prepared starting from 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (30 mg, 130 μmol) and (S)-2-hydroxy-N-(2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-3-methyl-phenoxy]-propyl)-acetamide (35 mg, 117 μmol) according to Method A; LC-MS: tR=0.50 min; [M+1]+=489.23.

Sources & evidence

ORD record
ord-de98dbf7566147cc90155afca109fa39
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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