4-Isobutyl-3,5-dimethylthiophene-2-carboxylic acid → 4-[5-(4-Isobutyl-3,5-dimethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol

HRID 1676148Notes

Reaction equation

HRID 1676148 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:14])=[C:7]([C:11]([OH:13])=O)[S:8][C:9]=1[CH3:10])[CH:2]([CH3:4])[CH3:3].[OH:15][C:16]1[C:25]([CH3:26])=[CH:24][C:19]([C:20]([NH:22]O)=[NH:21])=[CH:18][C:17]=1[CH3:27]>>[CH2:1]([C:5]1[C:6]([CH3:14])=[C:7]([C:11]2[O:13][N:22]=[C:20]([C:19]3[CH:24]=[C:25]([CH3:26])[C:16]([OH:15])=[C:17]([CH3:27])[CH:18]=3)[N:21]=2)[S:8][C:9]=1[CH3:10])[CH:2]([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 594978664-Isobutyl-3,5-dimethylthiophene-2-carboxylic acidHCID 178426654HCID 178426654, compound

Product 1

HCID 1361334304-[5-(4-Isobutyl-3,5-dimethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol

Procedure

4-[5-(4-Isobutyl-3,5-dimethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol is prepared from 4-isobutyl-3,5-dimethyl-thiophene-2-carboxylic acid and 4,N-dihydroxy-3,5-dimethyl-benzamidine in analogy to Example 21; LC-MS: tR=1.20 min, [M+1]=357.35; 1H NMR (D6-DMSO): δ 8.91 (s, 1H), 7.60 (s, 2H), 2.53 (s, 3H), 2.44-2.40 (m, 5H), 2.23 (s, 6H), 1.81-1.72 (m, 1H), 0.89 (d, J=6.4 Hz, 6H).

Sources & evidence

ORD record
ord-7236f024c3e744dea2374bcf831f86e1
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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