HCID 69446647, compound → HCID 69447979, compound

HRID 1592999Notes

Reaction equation

HRID 1592999 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH2:12][CH2:13]1

Participants

3

Reactant 1

HCID 69446647HCID 69446647, compound

Product 1

HCID 69447979HCID 69447979, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-4-(5-cyano-1H-benzimidazol-1-yl)piperidin-1-carboxylate (326 mg) was dissolved in DCM (10 ml) and silica gel (10 g) was added and the mixture evaporated to dryness. Toluene (100 ml) was added and the mixture refluxed for 15 hours. The mixture was evaporated to dryness and the silica was then washed with dichloromethane. The organics were evaporated to a gum which was purified by chromatography on silica eluting with NH3/MeOH/dichloromethane (2:18:80) to give the title compound as a solid. Yield 77 mg. NMR (d6 DMSO): 2.0 (m, 4H), 2.75 (m, 2H), 3.15 (m, 2H), 4.6 (m, 1H), 7.7 (d, 1H), 7.9 (d, 1H), 8.2 (s, 1H), 8.6 (s, 1H). MS 227 (MH+).

Workup

  1. additionsilica gel (10 g) was added
  2. customthe mixture evaporated to dryness
  3. additionToluene (100 ml) was added
  4. temperaturethe mixture refluxed for 15 hours
  5. customThe mixture was evaporated to dryness
  6. washthe silica was then washed with dichloromethane
  7. customThe organics were evaporated to a gum which
  8. customwas purified by chromatography on silica eluting with NH3/MeOH/dichloromethane (2:18:80)

Sources & evidence

ORD record
ord-813961970ab342c4923732465bad795e
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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