Dimethylformamide → HCID 178423480, compound

HRID 641071Notes

Reaction equation

HRID 641071 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:25]2[CH:24]=[C:23]([NH:28][C:10]([C:2]3[NH:1][C:5]4[CH:6]=[CH:7][C:8]([CH3:35])=[CH:9][C:4]=4[N:3]=3)=[O:12])[CH:22]=[CH:27][CH:26]=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 178423480HCID 178423480, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.064 mmol of benzimidazolecarboxylic acid 4k 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 4 hours, 0.3 eq. of acid was added, and the mixture was stirred overnight. After further addition of 0.3 eq. of acid, the reaction mixture was diluted with water after 2 hours, and the resulting precipitate was filtered off with suction and washed with water. The resulting crude product was purified by chromatography (ethyl acetate).

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationthe resulting precipitate was filtered off with suction
  3. washwashed with water
  4. customThe resulting crude product was purified by chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f9cac9b931a140bfa360ee2dfc436b3c
Source dataset
uspto-grants-2010_04
Patent number
US07691870B2

Reaction notes

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