Sodium Hydroxide → HCID 22989372, compound

HRID 1169085Notes

Reaction equation

HRID 1169085 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 adjusted 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. additionadjusted 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-fbe4813e2ac34880978b7b30f4a49430
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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