Sodium Bicarbonate → HCID 22989389, compound

HRID 1169111Notes

Reaction equation

HRID 1169111 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][NH2:26])[CH2:19][CH2:18]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[C:35]([C:37]([CH3:44])([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=2)[N:33]=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][NH:26][C:28]4[CH:29]=[CH:30][C:31]5[N:32]([CH:34]=[C:35]([C:37]([CH3:43])([CH3:44])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=5)[N:33]=4)[CH2:19][CH2:18]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoateHCID 22989289HCID 22989289, compound

Product 1

HCID 22989389HCID 22989389, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

1.69 g of 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-oxy)-1-piperidinepropanamine and 645 mg of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate were dissolved in 3 ml of 1-methyl-2-pyrrolidone, followed by stirring in an oil bath (170° C.) for 7 hours. After cooling, saturated aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with water and saturated saline, dried over magnesium sulfate. The solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (50:5:1). The desired fraction was collected, concentrated, the residue was subjected to silica gel column chromatography again and eluted with dichloromethane:methanol:triethylamine (100:1:2). The desired fraction was collected and concentrated to yield 340 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. washeluted with dichloromethane:methanol:triethylamine (100:1:2)
  10. customThe desired fraction was collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f299a7ee201c4662934557a51b6fd2db
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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