Water → 2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine

HRID 885429Notes

Reaction equation

HRID 885429 reaction equation
[CH2:1]([C:3]1[NH:13][C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[OH-].[Li+].[I-].[CH:17]1[C:27]2[CH2:26][CH2:25][C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[NH:22][C:21]=2[CH:20]=[CH:19][C:18]=1[CH2:32][N+]1(C)CCCCC1.O>CN(C=O)C>[CH2:1]([C:3]1[N:13]([CH2:32][C:18]2[CH:19]=[CH:20][C:21]3[NH:22][C:23]4[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=4[CH2:25][CH2:26][C:27]=3[CH:17]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 86608578HCID 86608578, compoundHCID 178437439HCID 178437439, compound

Product 1

HCID 199708722-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepineYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

[step 1] 2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (U.S. Pat. No. 5,332,744; 36.55 g, 209 mmol) was dissolved in DMF (365.5 mL), and the solution was added with lithium hydroxide (5.62 g, 235 mmol), followed by stirring at room temperature for 15 min. 1-(10,11-Dihydro-5H-dibenzo[b,f]azepin-2-ylmethyl)-1-methylpiperidinium iodide (JP-A-7-61983; 95.0 g, 219 mmol) and DMF (73.1 mL) were added thereto, and the mixture was stirred at 40° C. for 8 hr. After cooling to room temperature, water (175.4 mL) was added dropwise, and the mixture was stirred under ice-cooling for 2 hr. The precipitate was collected by filtration, and dissolved in chloroform (520 mL) with heating. Activated carbon (5.2 g) was added, and the mixture was stirred for 30 min with heating, and the hot solution was filtered. Ethyl acetate (1041 mL) was added to the filtrate, and the precipitate was collected by filtration to give 2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine (36.7 g, 46%).

Workup

  1. stirringthe mixture was stirred at 40° C. for 8 hr
  2. temperatureAfter cooling to room temperature
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 2 hr
  5. filtrationThe precipitate was collected by filtration
  6. dissolutiondissolved in chloroform (520 mL)
  7. temperaturewith heating
  8. additionActivated carbon (5.2 g) was added
  9. stirringthe mixture was stirred for 30 min
  10. temperaturewith heating
  11. filtrationthe hot solution was filtered
  12. additionEthyl acetate (1041 mL) was added to the filtrate
  13. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-0689f1fa6ba84a3bbe0e3418ae531813
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

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