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

HRID 1169091Notes

Reaction equation

HRID 1169091 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 adjusted 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 over magnesium sulfate and 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. additionadjusted to pH 5 by the addition of 1 N hydrochloric acid
  7. extractionextracted with tetrahydrofuran
  8. dry with materialthe extract was dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionpowdered by the addition of ethyl ether
  11. filtrationcollected by filtration
  12. customdried

Sources & evidence

ORD record
ord-cc2139f450d64c7eb580edd828f4eb50
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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