Dimethylformamide → HCID 178423478, compound

HRID 641077Notes

Reaction equation

HRID 641077 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=2[CH:40]=1.CC[N:47]([CH:51]([CH3:53])C)[CH:48]([CH3:50])C.[CH3:54]N(C=O)C>O>[N:47]1[CH:48]=[CH:50][C:35]([CH2:40][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][C:8]([CH3:54])=[CH:9][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 178423478HCID 178423478, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.064 mmol benzimidazole carboxylic acid 4k and 0.064 mmol amine 5e are dissolved together in DMF, treated consecutively with a solution of TBTU (0.096 mmol) in DMF, a solution of HOBT (0.026 mmol) in DMF and 0.32 mmol DIPEA, and stirred overnight at room temperature. After 4 h, further 0.3 eq. of the acid are added and the reaction mixture is stirred overnight. Finally, 2 hrs after a further addition of 0.3 eq. acid, the reaction mixture is diluted with water, the formed precipitate is separated by filtration by suction, rinsed with water and dried. The thus obtained crude product is purified by chromatography (ethyl acetate/n-heptane—8/2).

Workup

  1. customthe formed precipitate is separated by filtration by suction
  2. washrinsed with water
  3. customdried
  4. customThe thus obtained crude product
  5. customis purified by chromatography (ethyl acetate/n-heptane—8/2)

Sources & evidence

ORD record
ord-cfba87588f764a0091f2cc4e9649bd57
Source dataset
uspto-grants-2010_04
Patent number
US07691870B2

Reaction notes

Loading…