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

HRID 641072Notes

Reaction equation

HRID 641072 reaction equation
[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:16]([O:20]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:35]1[CH:36]=[CH:37][C:38]2[N:43](O)N=N[C:39]=2[CH:40]=1.CC[N:47]([CH:51]([CH3:53])C)[CH:48]([CH3:50])C>CN(C=O)C.O>[N:47]1[CH:48]=[CH:50][C:16]([O:20][C:36]2[CH:37]=[C:38]([NH:43][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:39]=[CH:40][CH:35]=2)=[CH:53][CH:51]=1

Participants

7

Reactant 4

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

Product 1

HCID 58858404N-{3-[(Pyridin-4-yl)oxy]phenyl}-1H-benzimidazole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

0.064 mmol of benzimidazolecarboxylic acid 4l was dissolved in DMF together with 0.064 mmol of the amine 5c, 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, 0.25 eq. of acid was added, and the mixture was stirred overnight. After further addition of 0.5 eq. of acid, the reaction mixture was diluted with water after 16 hours and extracted a number of times with ethyl acetate. The combined organic phases were washed 2× with water, dried, filtered and evaporated. The residue was digested with ethyl acetate/methanol (a little).

Workup

  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

Sources & evidence

ORD record
ord-c93a1a039026413b8b92289b5ad338f9
Source dataset
uspto-grants-2010_04
Patent number
US07691870B2

Reaction notes

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