5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → (2S)-3-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-3-methoxy-phenoxy}-propane-1,2-diol

HRID 1685790Notes

Reaction equation

HRID 1685790 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].CC1(C)[O:21][C@H:20]([CH2:22][O:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([NH:30]O)=[NH:29])=[C:26]([O:34][CH3:35])[CH:25]=2)[CH2:19][O:18]1>>[CH2:4]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:14][N:29]=[C:28]([C:27]3[CH:32]=[CH:33][C:24]([O:23][CH2:22][C@@H:20]([OH:21])[CH2:19][OH:18])=[CH:25][C:26]=3[O:34][CH3:35])[N:30]=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 178493524HCID 178493524, compound

Product 1

HCID 67265580(2S)-3-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-3-methoxy-phenoxy}-propane-1,2-diolYield 24.8%

Procedure

The title compound (13 mg) is prepared starting from 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (30 mg, 130 μmol) and (R)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-2-methoxy-benzamidine (35 mg, 117 μmol) in analogy to Example 197; LC-MS: tR=0.47 min; [M+1]+=448.09.

Sources & evidence

ORD record
ord-a42ae9b5f3c049c9a267ed88be7a7d70
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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