Water → HCID 69321088, compound

HRID 2217301Notes

Reaction equation

HRID 2217301 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.Cl[CH:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[N:28]1[C:27]2[CH:23]([N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[C:2]3[NH:10][CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH2:24][CH2:25][C:26]=2[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 14327172HCID 14327172, compound

Product 1

HCID 69321088HCID 69321088, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 4-(1H-benzimidazol-2-ylamino)-1-piperidine-carboxylate (0.0289 mol), 7-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.0289 mol) and potassium carbonate (0.0867 mol) in acetonitrile (250 ml) was stirred and refluxed for 48 hours and then brought to room temperature. The reaction was carried out again using the same quantities. The mixtures were combined, poured out into H2O and extracted with EtOAc. The organic layer was separated, washed with H2O, dried (MgSO4), filtered and the solvent was evaporated. The residue (25 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH NH4OH 97/3/0.5; 20-45 μm). Two fractions were collected and their solvents were evaporated, yielding 8 g of ethyl 4-[[1-(6,7-dihydro-5H-1-pyrindin-7-yl) 1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate (interm. 22).

Workup

  1. temperaturerefluxed for 48 hours
  2. custombrought to room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with H2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue (25 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH NH4OH 97/3/0.5; 20-45 μm)
  10. customTwo fractions were collected
  11. customtheir solvents were evaporated

Sources & evidence

ORD record
ord-0d259ff327e143a3a68d55e70155d72a
Source dataset
uspto-grants-2008_08
Patent number
US07407969B2

Reaction notes

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