N-(6-bromo-2-chloro-3-(methylamino)pyridin-4-yl)propionamide → 6-Bromo-4-chloro-2-ethyl-3-methyl-imidazo[4,5-c]pyridine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH3:10])=[C:4]([NH:11][C:12](=O)[CH2:13][CH3:14])[CH:3]=1>Cl.CC(O)=O>[Br:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]2[N:9]([CH3:10])[C:12]([CH2:13][CH3:14])=[N:11][C:4]=2[CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
N-(6-bromo-2-chloro-3-(methylamino)pyridin-4-yl)propionamide 2.78 (213 mg, 0.73 mmol) was dissolved in a mixture of HCl (37% aqueous solution) and AcOH 1:5 (12 mL) and the mixture was heated in a sealed tube at 100° C. After 2 h, LC/MS indicated full conversion to desired product. Reaction mixture was evaporated under reduced pressure. Solids were suspended and stirred for 10 min in a basic aqueous solution of NaHCO3 Solids were collected by filtration to isolate 6-bromo-4-chloro-2-ethyl-3-methyl-3H-imidazo[4,5-c]pyridine 2.79. LCMS found for C9H9BrClN3 as (M+H)+ 273.9.
Sources & evidence
- ORD record
- ord-24da1c7810ef4d2bb18b8cca3050c5e9
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
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