Dimethylformamide → HCID 86612164, compound

HRID 641064Notes

Reaction equation

HRID 641064 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]1C=CC2N(O)N=NC=2C=1.CC[N:47]([CH:51]([CH3:53])C)[CH:48]([CH3:50])C.CN([CH:57]=[O:58])C>O>[N:47]1[CH:48]=[CH:50][C:57]([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]=[C:9]([CH3:35])[C:4]=4[N:3]=3)=[O:12])=[CH:24][CH:25]=2)=[CH:53][CH:51]=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 86612164HCID 86612164, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.064 mmol of benzimidazolecarboxylic acid 4f 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 at room temperature. After 3 hours, a further 0.3 eq. of acid was added, and the mixture was stirred overnight. The reaction mixture was diluted with water, and the resulting precipitate was filtered off with suction and washed with water.

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-b72f0251ef9247ec84abbb0f6e710677
Source dataset
uspto-grants-2010_04
Patent number
US07691870B2

Reaction notes

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