Dimethylformamide → 3-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid

HRID 1513295Notes

Reaction equation

HRID 1513295 reaction equation
C[O:2][C:3]([C:5]([CH3:28])([CH3:27])[CH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:15][C:16]3[CH:22]=[C:21]([C:23]([OH:25])=O)[CH:20]=[CH:19][C:17]=3[N:18]=2)=[C:9]([CH3:26])[CH:8]=1)=[O:4].[NH2:29]C1C=C(C(O)=O)C=CC=1N.COC(=O)C(C)(C)[CH2:44][C:45]1[CH:50]=[C:49](C)[C:48](C=O)=[C:47](C)[CH:46]=1.OOS([O-])=O.[K+].C[N:65]([CH:67]=O)C>O>[CH3:13][C:11]1[CH:12]=[C:7]([CH2:6][C:5]([CH3:27])([CH3:28])[C:3]([OH:2])=[O:4])[CH:8]=[C:9]([CH3:26])[C:10]=1[C:14]1[NH:15][C:16]2[CH:22]=[C:21]([C:23]3[O:25][C:67]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=4[CH3:44])=[N:65][N:29]=3)[CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 692633,4-Diaminobenzoic acidHCID 23707502Potassium hydroxy sulfiteHCID 669667662-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl-phenyl]-3H-benzoimidazole-5-carboxylic acidHCID 86632822Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate

Product 1

HCID 252354593-{3,5-Dimethyl-4-[6-(5-o-tolyl-[1,3,4]oxadiazol-2-yl)-1H-benzoimidazol-2-yl]-phenyl}-2,2-dimethyl-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2-[4-(2-Methoxycarbonyl-2-methyl-propyl)-2,6-dimethyl -phenyl]-3H-benzoimidazole-5-carboxylic acid. 7.6 g of 3,4-diaminobenzenoic acid was stirred in 120 ml of DMF at room temperature. It was treated with 12.4 g of 3-(4-formyl-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester (the intermediate A in Example 1-62) followed by an addition of a slurry of 15 g of Oxone in 60 ml of DMF. The reaction was stirred at room temperature for 3 h and 60 mL of water was added and the pH was adjusted to 6. Additional 150 mL of water was added and the resulting precipitates were collected by filtration. The collected precipitates were washed with water and dried under vacuum to afford the title compound.

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. customThe collected precipitates
  4. washwere washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-42dacf1cf08b47f9b477799528c38d48
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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