Dimethylformamide → HCID 178482117, compound

HRID 81198Notes

Reaction equation

HRID 81198 reaction equation
[CH3:1]N(C=O)C.[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[C:18]3[N:19]([CH2:29][C@H:30]4[CH2:35][CH2:34][C@H:33]([CH3:36])[CH2:32][CH2:31]4)[C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:21][C:17]=3[CH:16]=[C:15]([C:37]#[N:38])[N:14]=2)[CH:10]=[N:11][CH:12]=1.CI.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[C:18]3[N:19]([CH2:29][C@H:30]4[CH2:35][CH2:34][C@H:33]([CH3:36])[CH2:32][CH2:31]4)[C:20]([N:22]([CH3:1])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:21][C:17]=3[CH:16]=[C:15]([C:37]#[N:38])[N:14]=2)[CH:10]=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178461248HCID 178461248, compound

Product 1

HCID 178482117HCID 178482117, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

DMF (4 mL) was added to a vial containing 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-(phenylamino)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (200 mg, 0.438 mmol), followed by methyl iodide (68 mg, 0.481 mmol) and potassium carbonate (121 mg, 0.877 mmol), and the vial was sealed and heated to 60° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 15% ethyl acetate/petroleum ether as eluent to afford 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[methyl(phenyl)amino]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ES/APCl calc'd. for C27H27ClN6 [M+H]+ 471. found 471.

Workup

  1. customthe vial was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c497206d8d642c489aed7d1a3fb78e7
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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