1-Hydroxybenzotriazole → 1H-Benzimidazole-2-carboxamide, N-[4-(4-pyridinyloxy)phenyl]-

HRID 641066Notes

Reaction equation

HRID 641066 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:35]2[CH:40]=[CH:39][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:37][CH:36]=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 111865451H-Benzimidazole-2-carboxamide, N-[4-(4-pyridinyloxy)phenyl]-

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 5a, 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 overnight at room temperature. A further 0.25 eq. of acid was added, and the mixture was stirred for 4 hours. 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.

Workup

  1. stirringthe mixture was stirred for 4 hours
  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-1e4cf4d23847450bbe6ccdc4380a391b
Source dataset
uspto-grants-2010_04
Patent number
US07691870B2

Reaction notes

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