5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → (2S)-3-{2-Chloro-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diol

HRID 1685789Notes

Reaction equation

HRID 1685789 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[C:33]([CH3:34])=[CH:32][C:27]([C:28]([NH:30]O)=[NH:29])=[CH:26][C:25]=2[Cl:35])[CH2:19][O:18]1>>[Cl:35][C:25]1[CH:26]=[C:27]([C:28]2[N:30]=[C:12]([C:10]3[S:11][C:7]([CH2:6][N:3]([CH2:1][CH3:2])[CH2:4][CH3:5])=[C:8]([CH3:15])[CH:9]=3)[O:14][N:29]=2)[CH:32]=[C:33]([CH3:34])[C:24]=1[O:23][CH2:22][C@@H:20]([OH:21])[CH2:19][OH:18]

Participants

3

Reactant 2

HCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178426667(R)-3-Chloro-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-5-methyl-benzamidine

Product 1

HCID 66829288(2S)-3-{2-Chloro-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diolYield 40.4%

Procedure

The title compound (22 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-3-chloro-5-methyl-benzamidine (37 mg, 117 μmol) in analogy to Example 197; LC-MS: tR=0.54 min; [M+1]+=466.05.

Sources & evidence

ORD record
ord-b76c7f79101a4d38a3af3e5de6567183
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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