Triphosgene → 1-methyl-1H,2H,3H-imidazo(4,5-c)pyridin-2-one

HRID 656842Notes

Reaction equation

HRID 656842 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][CH3:9].Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl>>[CH3:9][N:8]1[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[NH:1][C:11]1=[O:13]

Participants

3

Reactant 2

HCID 94429TriphosgeneHCID 9104124-N-methylpyridine-3,4-diamine

Product 1

HCID 122993531-methyl-1H,2H,3H-imidazo(4,5-c)pyridin-2-one

Procedure

To a stirred suspension of 3-amino-4-methylaminopyridine [U.S. Pat. No. 5,371,086 (1993)](190 mg, 1.54 mmol) in CH3 CN (10 mL) was added triphosgene (458 mg, 1.54 mmol) portionwise. After 1 h, the mixture was concentrated in vacuo and the residue was converted to the free base by ion exchange chromatography on a SCX cartridge, eluting with 2 M NH3 in MeOH to give the title compound. MS: m/z=150 (M+1).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. washeluting with 2 M NH3 in MeOH

Sources & evidence

ORD record
ord-9f53e98df9d94495b4a3d9739338975e
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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