N-(4-Cyanophenyl)glycine → 1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

HRID 50228Notes

Reaction equation

HRID 50228 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11](O)=O)=[CH:5][CH:4]=1)#[N:2].[C:14]1([N:20]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:21](=[O:31])[C:22]2[CH:27]=[CH:26][C:25]([NH:28][CH3:29])=[C:24]([NH2:30])[CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[C:14]1([N:20]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:21]([C:22]2[CH:27]=[CH:26][C:25]3[N:28]([CH3:29])[C:11]([CH2:10][NH:9][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=4)=[N:30][C:24]=3[CH:23]=2)=[O:31])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 817965N-(4-Cyanophenyl)glycineHCID 184123283-Amino-4-methylaminobenzoic acid-n-phenyl-n-(2-ethoxycarbonylethyl)amide

Product 1

HCID 184125221-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.17 g (0.035 mol) of N-(4-cyanophenyl)glycine and 5.68 g (0.035 mol) of N,N′-carbonyldiimidazole were refluxed in 300 mL of tetrahydrofuran for 30 minutes, then 10.6 g (0.032 mol) of 3-amino-4-methylaminobenzoic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide were added, and the mixture was refluxed for a further five hours. Then the solvent was distilled off in vacuo, the residue was dissolved in 150 mL of glacial acetic acid and refluxed for one hour. Then the glacial acetic acid was distilled off in vacuo, the residue was dissolved in about 300 mL of dichloromethane, the solution was washed twice with about 150 mL water and then dried over sodium sulfate. After evaporation of the solvent, the crude product thus obtained was purified by column chromatography (800 g silica gel; eluant: dichloromethane with 1-2% ethanol). Yield: 8.5 g (57% of theory); Rf value: 0.51 (silica gel; dichloromethane/ethanol=19:1).

Workup

  1. temperaturethe mixture was refluxed for a further five hours
  2. distillationThen the solvent was distilled off in vacuo
  3. dissolutionthe residue was dissolved in 150 mL of glacial acetic acid
  4. temperaturerefluxed for one hour
  5. distillationThen the glacial acetic acid was distilled off in vacuo
  6. dissolutionthe residue was dissolved in about 300 mL of dichloromethane
  7. washthe solution was washed twice with about 150 mL water
  8. dry with materialdried over sodium sulfate
  9. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-42618ef578b84b34a610848fb5389fae
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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