5-Formyl-4-methylthiophene-2-carboxylic acid → Rac-5-{3-[4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3,5-dimethyl-phenyl]-[1,2,4]oxadiazol-5-yl}-3-methyl-thiophene-2-carbaldehyde

HRID 1685736Notes

Reaction equation

HRID 1685736 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][C:4]=1[CH3:11])=[O:2].[CH3:12][C:13]1([CH3:32])[O:17][CH:16]([CH2:18][O:19][C:20]2[C:29]([CH3:30])=[CH:28][C:23]([C:24]([NH:26]O)=[NH:25])=[CH:22][C:21]=2[CH3:31])[CH2:15][O:14]1>>[CH3:12][C:13]1([CH3:32])[O:17][CH:16]([CH2:18][O:19][C:20]2[C:21]([CH3:31])=[CH:22][C:23]([C:24]3[N:26]=[C:8]([C:6]4[S:7][C:3]([CH:1]=[O:2])=[C:4]([CH3:11])[CH:5]=4)[O:10][N:25]=3)=[CH:28][C:29]=2[CH3:30])[CH2:15][O:14]1

Participants

3

Reactant 2

HCID 532126825-Formyl-4-methylthiophene-2-carboxylic acidHCID 178426655HCID 178426655, compound

Product 1

HCID 87330589Rac-5-{3-[4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3,5-dimethyl-phenyl]-[1,2,4]oxadiazol-5-yl}-3-methyl-thiophene-2-carbaldehyde

Procedure

The title compound is prepared according to Method A starting from 5-formyl-4-methyl-thiophene-2-carboxylic acid and rac-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-3,5-dimethyl-benzamidine; LC-MS: tR=1.16 min; [M+1]+=429.16; 1H NMR (D6-DMSO): δ1.34 (s, 3H), 1.38 (s, 3H), 2.34 (s, 6H), 2.65 (s, 3H), 3.79-3.93 (m, 3H), 4.10-4.15 (m, 1H), 4.42-4.49 (m, 1H), 7.75 (s, 2H), 8.07 (s, 1H), 10.17 (s, 1H).

Sources & evidence

ORD record
ord-609d6a38ace44c37afa337bbc1939ebd
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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