Diisopropylamine → HCID 178509145, Verbindung

HRID 278034

Reaktionsgleichung

Reaktionsgleichung von HRID 278034
[NH2:1][CH:2]([C:11]1[O:15][C:14]([NH2:16])=[N:13][N:12]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:32](O)=[O:33])=[CH:31][C:25]=3[N:24]=2)=[CH:19][CH:18]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(NC(C)C)(C)C>CN(C)C=O>[NH2:16][C:14]1[O:15][C:11]([CH:2]([NH:1][C:32]([C:30]2[CH:29]=[CH:28][C:26]3[NH:27][C:23]([C:20]4[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=4)=[N:24][C:25]=3[CH:31]=2)=[O:33])[CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:12][N:13]=1

Komponenten

6

Edukt 4

HCID 7912DiisopropylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226269395-(1-Amino-3-phenylpropyl)-[1,3,4]oxadiazol-2-ylamineHCID 178524160HCID 178524160, Verbindung

Produkt 1

HCID 178509145HCID 178509145, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.18 g of 5-(1-amino-3-phenylpropyl)-[1,3,4]oxadiazol-2-ylamine was dissolved in 10 ml of dry dimethylformamide at RT, treated with 200 mg of 2-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid, 270 mg of TOTU, and 0.12 ml of diisopropylamine, and stirred at RT for 4 h. The reaction mixture was concentrated, and the residue was taken up in ethyl acetate and washed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The residue was stirred with methyl tert-butyl ether, filtered off, and dried under high vacuum. 2-Pyridin4-yl-1H-benzimidazole-5-carboxylic acid [1-(5-amino-[1,3,4]oxadiazol-2-yl)-3-phenylpropyl]amide, which melts at 160° C. with decomposition, is obtained.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. washwashed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringThe residue was stirred with methyl tert-butyl ether
  7. filtrationfiltered off
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f71fbc6784cd47cc9dde6ac5c08115e2
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358978B1

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