Acetonitrile → 4-Amino-1,3-dihydro-6,7-dimethyl-1-(phenylmethyl)-2H-imidazo[4,5-c]pyridin-2-one

HRID 639595Notes

Reaction equation

HRID 639595 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15]([CH3:17])=[C:14]([CH3:18])[N:13]=[C:12]([N:19](CC=C)CC=C)[C:11]=2[NH:10][C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C>O>[CH2:1]([N:8]1[C:16]2[C:15]([CH3:17])=[C:14]([CH3:18])[N:13]=[C:12]([NH2:19])[C:11]=2[NH:10][C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 67456171HCID 67456171, compound

Product 1

HCID 497716454-Amino-1,3-dihydro-6,7-dimethyl-1-(phenylmethyl)-2H-imidazo[4,5-c]pyridin-2-oneYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Benzyl-4-diallylamino-6,7-dimethyl-1,3-dihydro-imidazo[4,5-c]pyridin-2-one (358 mg, 1 mmol) was taken up in water (10 mL) and acetonitrile (25 mL) and RhCl(PPh3)3 (286 mg, 0.3 mmol) was added in one portion and the mixture then heated at reflux for 16 h. The mixture was allowed to cool to room temperature, and then concentrated in vacuo, and the residue purified by column chromatography on silica gel using a gradient of 95:5→85:15 DCM:MeOH to afford the title compound as a pale brown solid (77 mg, 29%).

Workup

  1. temperaturethe mixture then heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by column chromatography on silica gel using a gradient of 95:5→85:15 DCM

Sources & evidence

ORD record
ord-1095d29f52144e10b0578133cd354a61
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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