Dichloromethane → 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile
Reaction equation
[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([Cl:10])=[CH:6][C:7]=1[NH:8][CH3:9].[CH2:13](Cl)Cl>C(O)(=O)C.C(OCC)(OCC)OCC.C(OCC)(=O)C>[Cl:10][C:5]1[N:4]=[C:3]([C:11]#[N:12])[C:2]2[N:1]=[CH:9][N:8]([CH3:13])[C:7]=2[CH:6]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 150 °C
Procedure
The suspension of 3-amino-6-chloro-4-methylamino-pyridine-2-carbonitrile (1.8 g) in DCM (5 ml), acetic acid (1.5 ml) and triethyl orthoformate (10 ml) was heated in microwave at 150° C. for 30 minutes. The mixture was then diluted with ethyl acetate (200 ml), washed with 10% sodium carbonate (100 ml), dried over sodium sulphate, solvent removed under reduced pressure, DCM (5 ml) was then added to the residue, some product crashed out and collected by filtration (0.5 g), the rest was then columned on silica gel using ethyl acetate-heptane (55:45) as eluant to give another 0.8 g expected product (a total of 1.3 g product).
Workup
- washwashed with 10% sodium carbonate (100 ml)
- dry with materialdried over sodium sulphate, solvent
- customremoved under reduced pressure, DCM (5 ml)
- additionwas then added to the residue
- filtrationcollected by filtration (0.5 g)
Sources & evidence
- ORD record
- ord-9cb56772444849cc84a05a4b26c7e5b7
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932251B2
Reaction notes
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