Methanol → HCID 24765416, compound

HRID 639593Notes

Reaction equation

HRID 639593 reaction equation
C([NH:4][C:5]1[C:10]2[NH:11][C:12](=[O:21])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]=2[CH:8]=[C:7]([CH:22]2[CH2:24][CH2:23]2)[N:6]=1)C=C.B(F)(F)F.CCOCC.C(Cl)Cl.CO>C(O)C.[Pd]>[NH2:4][C:5]1[C:10]2[NH:11][C:12](=[O:21])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]=2[CH:8]=[C:7]([CH:22]2[CH2:23][CH2:24]2)[N:6]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 25208983HCID 25208983, compound

Product 1

HCID 24765416HCID 24765416, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Allylamino-1-Benzyl-6-cyclopropyl-1,3-dihydro-imidazo[4,5-c]pyridin-2-one (70 mg, 0.2 mmol) was dissolved in ethanol (2 mL) and 10% Pd—C (70 mg, w/w) was added followed by dropwise addition of BF3.OEt2 (27 □l, 0.2 mmol). The mixture was heated at reflux under N2 overnight. The mixture was allowed to cool to room temperature and filtered through arbocel, rinsing with fresh EtOH and the filtrate was concentrated in vacuo to give the crude (150 mg). Column chromatography through silica eluting with 98:2→95:5 DCM:MeOH gave the title compound (17 mg) as an off white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under N2 overnight
  3. filtrationfiltered through arbocel
  4. washrinsing with fresh EtOH
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give the crude (150 mg)

Sources & evidence

ORD record
ord-ff4a09daaf164521a5bf8f3cc3615a9d
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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