Dimethylformamide → 5-chloro-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

HRID 629857Notes

Reaction equation

HRID 629857 reaction equation
[Cl:1][C:2]1[N:7]=C(NC)[C:5]([NH2:10])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:23][N:24]([CH:26]=[O:27])[CH3:25]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:7]=[C:23]2[N:24]([CH3:25])[C:26](=[O:27])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 249039426-Chloro-N2-methylpyridine-2,3-diamine

Product 1

HCID 552690615-chloro-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloro-N2-methylpyridine-2,3-diamine (1-2, 35 g, 222 mmol) and 1,1′-carbonyldiimidazole (63 g, 389 mmol) were added to a round bottom flask and suspended in DMF (150 mL). The solution was heated to 80° C. in an oil bath overnight. The reaction was then suspended in ethyl acetate and sodium bicarbonate. The suspension was washed with sodium bicarbonate, brine(×5), dried over sodium sulfate, filtered, and concentrated to produce 5-chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3) as a white solid. HRMS (M+H)+: observed=184.0279, calculated=184.0272.

Workup

  1. washThe suspension was washed with sodium bicarbonate, brine(×5)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae42e4ad48f44996b139c6fee122ebdb
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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