Triethylamine → N,N,2-Trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide

HRID 2239290Notes

Reaction equation

HRID 2239290 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:19]([OH:21])=O)[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1.Cl.[CH3:23][NH:24][CH3:25].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.CO>[CH3:23][N:24]([CH3:25])[C:19]([C:8]1[CH:9]=[C:10]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4]2[N:3]=[C:2]([CH3:1])[NH:6][C:5]=2[CH:7]=1)=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 685745314-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid

Product 1

HCID 68574634N,N,2-Trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamideYield 89.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 2-methyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxylic acid (5.0 g, 17.7 mmol, STEP 4), dimethylamine hydrochloride (4.33 g, 53.1 mmol), 2-[1H-benzotriazole-1-yl]-1,1,3,3-tetramethyluronium hexafluorophosphate (10.1 g, 26.6 mmol), and triethylamine (10.7 g, 106 mmol) in N,N-dimethylformamide (80 mL) was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate/methanol (20:1), and washed with saturated ammonium chloride aqueous solution. The organic layer was dried over magnesium sulfate, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (gradient elution from ethyl acetate only to ethyl acetate methanol 5:1) to afford the title compound as a white solid (4.90 g, 89%).

Workup

  1. washwashed with saturated ammonium chloride aqueous solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified by column chromatography on silica gel (
  5. washgradient elution from ethyl acetate only to ethyl acetate methanol 5:1)

Sources & evidence

ORD record
ord-564ba6cec721409a9bbe4db84d6ea342
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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