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

HRID 1067540Notes

Reaction equation

HRID 1067540 reaction equation
Cl.Cl.[Cl:3][C:4]1[N:8]2[N:9]=[C:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([O:23][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)[CH2:19][CH2:18]3)[CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:37]([CH3:44])([CH3:43])[C:38]([O:40]CC)=[O:39].[OH-].[Na+]>C(O)C>[Cl:3][C:4]1[N:8]2[N:9]=[C:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][CH:20]([O:23][CH:24]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:21][CH2:22]3)[CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:37]([CH3:44])([CH3:43])[C:38]([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22989228Ethyl 2-[3-chloro-6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate dihydrochloride

Product 1

HCID 229893252-[3-Chloro-6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionic AcidYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

653 mg of ethyl 2-[3-chloro-6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate dihydrochloride was dissolved in 6 ml of ethanol; 1.97 ml of a 2 N aqueous solution of sodium hydroxide was added, followed by thermal refluxing for 2.5 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 4.5 by the addition of 1 N hydrochloric acid. Acetone was added; the crystal precipitated was collected by filtration, washed with water-acetone (5:1) and dried to yield 465 mg of the title compound.

Workup

  1. customrefluxing for 2.5 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 4.5 by the addition of 1 N hydrochloric acid
  7. additionAcetone was added
  8. customthe crystal precipitated
  9. filtrationwas collected by filtration
  10. washwashed with water-acetone (5:1)
  11. customdried

Sources & evidence

ORD record
ord-8f60ff744ea749948c03fdefb544d6eb
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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