Sodium Bicarbonate → HCID 22989417, compound

HRID 1169092Notes

Reaction equation

HRID 1169092 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([CH:32]=[C:33]([C:35]([CH2:43][CH3:44])([CH2:41][CH3:42])[C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:34]=2)[N:31]=1.C(=O)(O)[O-].[Na+]>C(O)C>[ClH:25].[ClH:25].[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:26]3[CH:27]=[CH:28][C:29]4[N:30]([CH:32]=[C:33]([C:35]([CH2:41][CH3:42])([CH2:43][CH3:44])[C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:34]=4)[N:31]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 22989233HCID 22989233, compound

Product 1

HCID 22989417HCID 22989417, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

3.03 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 1.38 g of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylbutyrate were stirred at 160° C. for 1.5 hours, then at 180° C. for 2 hours. After the mixture was cooled to 90° C., ethanol and aqueous sodium bicarbonate were added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (100:5:2). The desired fraction was collected, concentrated under reduced pressure and dissolved in 5 ml of ethyl acetate; 1.4 ml of a 4 N solution of hydrogen chloride in ethyl acetate was added, followed by concentration again. The residue was powdered by the addition of ethyl ether and dried to yield 893 mg of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe extract was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate:methanol:triethylamine (100:5:2)
  6. customThe desired fraction was collected
  7. concentrationconcentrated under reduced pressure
  8. dissolutiondissolved in 5 ml of ethyl acetate
  9. addition1.4 ml of a 4 N solution of hydrogen chloride in ethyl acetate was added
  10. concentrationfollowed by concentration again
  11. additionThe residue was powdered by the addition of ethyl ether
  12. customdried

Sources & evidence

ORD record
ord-9bf2c05b76a642a59de5096e4c6dd785
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

Loading…