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

HRID 641075Notes

Reaction equation

HRID 641075 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:25]2[CH:24]=[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:22]=[CH:27][CH:26]=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 58858401N-{3-[(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 5d, 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. After further addition of 0.2 eq. of acid, the reaction mixture was diluted with water after 3 hours, and the resulting precipitate was filtered off with suction, washed with water and digested with diethyl ether.

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationthe resulting precipitate was filtered off with suction
  3. washwashed with water

Sources & evidence

ORD record
ord-430ad18557a8458f922875c5f737c547
Source dataset
uspto-grants-2010_04
Patent number
US07691870B2

Reaction notes

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