Homoveratrylamine → 1-Cyclohexyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(2-pyridinyl)-1H-benzimidazole-5-carboxamide

HRID 2116997Notes

Reaction equation

HRID 2116997 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([OH:18])=O)=[CH:15][C:10]=3[N:9]=[C:8]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:30][CH2:31][NH2:32].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH2:30][CH2:31][NH:32][C:16]([C:14]2[CH:13]=[CH:12][C:11]3[N:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[C:8]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[N:9][C:10]=3[CH:15]=2)=[O:18])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

7

Reactant 5

HCID 8421HomoveratrylamineHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 491114HCID 491114, compoundHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 5138911-Cyclohexyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(2-pyridinyl)-1H-benzimidazole-5-carboxamideYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Cyclohexyl-2-pyridin-2-yl-1H-benzoimidazole-5-carboxylic acid (0.060 g, 0.19 mmol), 3,4-dimethoxyphenethylamine (35 μL, 0.21 mmol) and TBTU (0.090 g, 0.28 mmol) were dissolved in DMF (1 mL), and DIEA (330 μL, 1.9 mmol) was added. The mixture was stirred 1 h at room temperature, when HPLC analysis indicated completion of the coupling reaction. The reaction mixture was added drop-wise with vigorous stirring to 1 N NaOH (10 mL). The precipitated product was collected by filtration, washed with water and dried. The title amide derivative was obtained as a gray solid (0.056 g, 60% yield, 98% homogeneity by HPLC).

Workup

  1. customcompletion of the coupling reaction
  2. additionThe reaction mixture was added drop-wise
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-19a271450ea0436f89387eb3d1f05c7d
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

Loading…