Sodium Hydroxide → 2-[6-[3-[4-(Diphenylmethylamino)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionic Acid

HRID 1067557Notes

Reaction equation

HRID 1067557 reaction equation
[C:1]1([CH:7]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][NH:24][C:25]3[CH:26]=[CH:27][C:28]4[N:29]([CH:31]=[C:32]([C:34]([CH3:41])([CH3:40])[C:35]([O:37]CC)=[O:36])[N:33]=4)[N:30]=3)[CH2:17][CH2:16]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH:7]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][NH:24][C:25]3[CH:26]=[CH:27][C:28]4[N:29]([CH:31]=[C:32]([C:34]([CH3:41])([CH3:40])[C:35]([OH:37])=[O:36])[N:33]=4)[N:30]=3)[CH2:17][CH2:16]2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22989234Ethyl 2-[6-[3-[4-(diphenylmethylamino) piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate

Product 1

HCID 229893972-[6-[3-[4-(Diphenylmethylamino)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionic AcidYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

612 mg of ethyl 2-[6-[3-[4-(diphenylmethylamino) piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate was dissolved in 5 ml of ethanol; 2.2 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by thermal refluxing for 6 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was diluted with water, washed with ethyl acetate and ajusted to pH 5 by the addition of 1 N hydrochloric acid. The mixture was saturated with sodium chloride and extracted with tetrahydrofuran; the extract was dried with magnesium sulfate. The dry product was concentrated under reduced pressure, powdered by the addition of ethyl ether, collected by filtration and dried to yield 503 mg of the title compound.

Workup

  1. customrefluxing for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. washwashed with ethyl acetate
  6. additionajusted to pH 5 by the addition of 1 N hydrochloric acid
  7. extractionextracted with tetrahydrofuran
  8. dry with materialthe extract was dried with magnesium sulfate
  9. concentrationThe dry product was concentrated under reduced pressure
  10. additionpowdered by the addition of ethyl ether
  11. filtrationcollected by filtration
  12. customdried

Sources & evidence

ORD record
ord-f2e62cff532549718cbbf56ecb956dff
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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