Triethylamine → 2-(2,6-Dichlorophenyl)-3H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-amide

HRID 1513227Notes

Reaction equation

HRID 1513227 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19](Cl)=[O:20])[CH:16]=[CH:15][C:13]=2[N:14]=1.C([N:24]([CH2:27][CH3:28])CC)C.C([O:32][CH2:33][CH3:34])(=O)C>C1COCC1>[Cl:1][C:3]1[CH:8]=[CH:7][C:34]([C:33](=[O:32])[CH:27]([NH:24][C:19]([C:17]2[CH:16]=[CH:15][C:13]3[N:14]=[C:10]([C:4]4[C:3]([Cl:2])=[CH:8][CH:7]=[CH:6][C:5]=4[Cl:9])[NH:11][C:12]=3[CH:18]=2)=[O:20])[CH3:28])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 866328172-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride

Product 1

HCID 669655372-(2,6-Dichlorophenyl)-3H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of1-(4-chlorophenyl)-2-aminopropiophenone hydrochloride (365 mg, 1.66 mmol), 2-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride (600 mg, 1.66 mmol) (Example 1-27, step E), and triethylamine (924 μL, 671 mg, 6.63 mmol) in THF (25 mL) was stirred at RT for 18 hrs. The solution was poured into ethyl acetate and extracted with water and brine. The organic layer was dried, filtered, and the solvent removed under reduced pressure. The residue was chromatographed using a gradient of 50-90% heptane/ethyl acetate to give the title compound.). MS: m/z 473.9 (M+1); H1-NMR (acetone-d6): δ 8.57 (m, broad, 1H), 8.37 (m, 3H), 8.11 (m, broad, 1H), 7.83 (m, 5H), 5.92 (quintet, J=7.2 Hz, 1H), 1.75 (d, J=7.0 Hz, 3H).

Workup

  1. extractionextracted with water and brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-db7e4f3026c64f5c8e25374773b85d98
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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