Sodium Hydroxide → HCID 22989372, compound

HRID 1067551Notes

Reaction equation

HRID 1067551 reaction equation
Cl.Cl.[C:3]1([CH:9]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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:33]([O:35]C(C)C)=[O:34])[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:39]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:33]([OH:35])=[O:34])[CH2:31][CH2:32]5)[N:29]=4)[N:26]=3)[CH2:15][CH2:16]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22989223HCID 22989223, compound

Product 1

HCID 22989372HCID 22989372, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

554 mg of isopropyl 1-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxylate dihydrochloride was dissolved in 3 ml of ethanol; 1.73 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, washed with ethyl acetate and ajusted to pH 5.5 by the addition of 1 N hydrochloric acid. The mixture was crystallized by the addition of acetone, washed with acetone and dried to yield 321 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. additionajusted to pH 5.5 by the addition of 1 N hydrochloric acid
  7. customThe mixture was crystallized by the addition of acetone
  8. washwashed with acetone
  9. customdried

Sources & evidence

ORD record
ord-8a79299aea71403e9a21f8adc6c744f9
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

Loading…