Methanol → HCID 25208983, compound

HRID 639617Notes

Reaction equation

HRID 639617 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[C:14]([CH:17]3[CH2:19][CH2:18]3)[N:13]=[C:12](Cl)[C:11]=2[NH:10][C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.CO>C(N)C=C.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([NH:8][C:12]1[C:11]2[NH:10][C:9](=[O:21])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]=2[CH:15]=[C:14]([CH:17]2[CH2:19][CH2:18]2)[N:13]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 86614470HCID 86614470, compound

Product 1

HCID 25208983HCID 25208983, compoundYield 151.9%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalyst2×HCID 7853AllylamineSolvent2×

Conditions

Temperature
85 °C

Procedure

1-Benzyl-4-chloro-6-cyclopropyl-1,3-dihydro-imidazo[4,5-c]pyridin-2-one (100 mg, 0.3 mmol) was dissolved in allylamine (2 mL) in a Reactivial™. Copper (II) sulphate (83 mg, 0.3 mmol) was added and the vial was sealed. The mixture was heated at 85° C. overnight. Further portions of copper (II) sulphate (83 mg, 0.3 mmol) and allylamine (1 mL) were added and the vial was sealed once again. The mixture was heated at 85° C. over the weekend. The mixture was allowed to cool to room temperature. The excess allylamine was removed in vacuo and the residue was dissolved in EtOAc (50 mL) and treated with saturated aqueous NaHCO3 (20 mL). The layers were separated and the organics washed with more saturated aqueous NaHCO3 (10 mL), then brine (10 mL), dried over MgSO4 and concentrated in vacuo to give the crude product (120 mg). Column chromatography through silica gel eluting with 98:2 DCM:MeOH gave the title compound (73 mg) as an off white solid.

Workup

  1. customthe vial was sealed
  2. customthe vial was sealed once again
  3. temperatureThe mixture was heated at 85° C. over the weekend
  4. temperatureto cool to room temperature
  5. customThe excess allylamine was removed in vacuo
  6. dissolutionthe residue was dissolved in EtOAc (50 mL)
  7. additiontreated with saturated aqueous NaHCO3 (20 mL)
  8. customThe layers were separated
  9. washthe organics washed with more saturated aqueous NaHCO3 (10 mL)
  10. dry with materialbrine (10 mL), dried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customto give the crude product (120 mg)

Sources & evidence

ORD record
ord-6a2c7e9d6849406d8a0840cd6b9b87b2
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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