Sodium Hydroxide → 2-[3-Chloro-6-[3-[4-(diphenylmethyl) piperazino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionic acid

HRID 1067538Notes

Reaction equation

HRID 1067538 reaction equation
Cl.Cl.Cl.[Cl:4][C:5]1[N:9]2[N:10]=[C:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:20][CH2:19]3)[CH:12]=[CH:13][C:8]2=[N:7][C:6]=1[C:37]([CH3:44])([CH3:43])[C:38]([O:40]CC)=[O:39].[OH-].[Na+]>C(O)C>[Cl:4][C:5]1[N:9]2[N:10]=[C:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][N:21]([CH:24]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:22][CH2:23]3)[CH:12]=[CH:13][C:8]2=[N:7][C:6]=1[C:37]([CH3:44])([CH3:43])[C:38]([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22989265Ethyl 2-[3-chloro-6-[3-[4-(diphenylmethyl)piperazino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate trihydrochloride

Product 1

HCID 229892372-[3-Chloro-6-[3-[4-(diphenylmethyl) piperazino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

633 mg of ethyl 2-[3-chloro-6-[3-[4-(diphenylmethyl)piperazino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate trihydrochloride was dissolved in 6 ml of ethanol; 2.31 ml of a 2 N aqueous solution of sodium hydroxide was added, followed by thermal refluxing for 1.5 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was diluted with water and washed with ethyl acetate; the water layer was ajusted to pH 5 by the addition of 1 N hydrochloric acid. Methanol was added; the crystal precipitated was collected by filtration, washed with water-ethyl acetate and dried to yield 462 mg of the title compound.

Workup

  1. customrefluxing for 1.5 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. additionthe water layer was ajusted to pH 5 by the addition of 1 N hydrochloric acid
  7. additionMethanol was added
  8. customthe crystal precipitated
  9. filtrationwas collected by filtration
  10. washwashed with water-ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-832078578235487bbf0f8b3262248ca3
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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