Sodium Hydroxide → HCID 22989247, compound

HRID 1067548Notes

Reaction equation

HRID 1067548 reaction equation
Cl.Cl.[C:3]1([CH:9]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][NH:20][C:21]3[CH:22]=[CH:23][C:24]4[N:25]([CH:27]=[C:28]([C:30]5([C:35]([O:37]C(C)C)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]5)[N:29]=4)[N:26]=3)[CH2:13][CH2:12]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[C:41]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][NH:20][C:21]3[CH:22]=[CH:23][C:24]4[N:25]([CH:27]=[C:28]([C:30]5([C:35]([OH:37])=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]5)[N:29]=4)[N:26]=3)[CH2:15][CH2:16]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22989212HCID 22989212, compound

Product 1

HCID 22989247HCID 22989247, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

598 mg of isopropyl 1-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]cyclopentanecarboxylate dihydrochloride was dissolved in 3 ml of ethanol; 2.24 ml of a 2 N aqueous solution of sodium hydroxide was added, followed by thermal refluxing for 7 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was diluted with water, washed with ethyl acetate and ajusted to pH 4.5 by the addition of 1 N hydrochloric acid. The mixture was saturated with sodium chloride and extracted with ethyl acetate-tetrahydrofuran (1:2); the extract was dried with magnesium sulfate. The dry product was concentrated under reduced pressure, powdered by the addition of ethyl acetate-ethyl ether (1:1), washed with ethyl ether and dried to yield 349 mg of the title compound.

Workup

  1. customrefluxing for 7 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 4.5 by the addition of 1 N hydrochloric acid
  7. extractionextracted with ethyl acetate-tetrahydrofuran (1:2)
  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 acetate-ethyl ether (1:1)
  11. washwashed with ethyl ether
  12. customdried

Sources & evidence

ORD record
ord-785d1a7272d2400895d87110da99df7e
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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