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 1513295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513295
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

Komponenten

7

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-42dacf1cf08b47f9b477799528c38d48
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217065B2

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