Sodium Hydroxide → HCID 22989358, compound

HRID 1067541Notes

Reaction equation

HRID 1067541 reaction equation
Cl.Cl.Cl.[Cl:4][C:5]1[N:9]2[N:10]=[C:11]([O: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+]>CC(O)C>[Cl:4][C:5]1[N:9]2[N:10]=[C:11]([O: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 Hydroxide2×HCID 22989423HCID 22989423, compound

Product 1

HCID 22989358HCID 22989358, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

458 mg of ethyl 2-[3-chloro-6-[3-[4-(diphenylmethyl)piperazino]propoxy]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate trihydrochloride was dissolved in 4 ml of 2-propanol; 1.34 ml of a 2 N aqueous solution of sodium hydroxide was added, followed by stirring at 80° C. for 1.5 hours, after which 0.3 ml of a 2 N aqueous solution of sodium hydroxide was added, followed by thermal refluxing for 2 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 by the addition of 1 N hydrochloric acid, followed by extraction with ethyl acetate; the extract was dried with sodium sulfate. The dry product was concentrated under reduced pressure and crystallized by the addition of ethyl acetate-ethyl ether-hexane (2:5:1), collected by filtration, washed with ethyl ether and dried to yield 125 mg of the title compound.

Workup

  1. customrefluxing for 2 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 by the addition of 1 N hydrochloric acid
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialthe extract was dried with sodium sulfate
  9. concentrationThe dry product was concentrated under reduced pressure
  10. customcrystallized by the addition of ethyl acetate-ethyl ether-hexane (2:5:1)
  11. filtrationcollected by filtration
  12. washwashed with ethyl ether
  13. customdried

Sources & evidence

ORD record
ord-46c5180577f24daab0ae435ebf35c9e0
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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