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

HRID 641069Notes

Reaction equation

HRID 641069 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(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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

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-69307ef932164e5c93bcd40d0d69f99a
Source dataset
uspto-grants-2010_04
Patent number
US07691870B2

Reaction notes

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