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Dimethylformamide → N-{4-[(Pyridin-3-yl)oxy]phenyl}-1H-benzimidazole-2-carboxamide

HRID 641069
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 641069
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]([OH:12])=O.CN(C(ON1N=[N:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:35]1[CH:36]=[CH:37]C2N(O)N=[N:41][C:39]=2[CH:40]=1.CCN(C(C)C)C(C)C.CN(C=[O:58])C>O>[N:41]1[CH:37]=[CH:36][CH:35]=[C:40]([O:58][C:26]2[CH:27]=[CH:22][C:23]([NH:28][C:10]([C:2]3[NH:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[O:12])=[CH:24][CH:25]=2)[CH:39]=1
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Komponenten

7

Edukt 5

HCID 6228Dimethylformamide3×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 58858400
N-{4-[(Pyridin-3-yl)oxy]phenyl}-1H-benzimidazole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

0.064 mmol of benzimidazolecarboxylic acid 4l was dissolved in DMF together with 0.064 mmol of the amine 5b, a solution of TBTU (0.096 mmol) in DMF, HOBT (0.026 mmol) in DMF and 0.32 mmol of DIPEA were added successively, and the mixture was stirred at room temperature. After 2.5 hours, 0.2 eq. of acid was added, and the mixture was stirred overnight. The reaction mixture was diluted with water and extracted a number of times with ethyl acetate. The combined organic phases were washed 2× with water, dried, filtered and evaporated.

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. extractionextracted a number of times with ethyl acetate
  3. washThe combined organic phases were washed 2× with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-69307ef932164e5c93bcd40d0d69f99a
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691870B2

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