Sodium Hydroxide → [6-[3-[4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-7-yl]carboxylic acid

HRID 1169101Notes

Reaction equation

HRID 1169101 reaction equation
[C:1]1([CH:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[C:20]([C:28]([O:30]C)=[O:29])=[CH:21][C:22]4[N:23]([N:25]=[CH:26][N:27]=4)[N:24]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:32]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[C:20]([C:28]([OH:30])=[O:29])=[CH:21][C:22]4[N:23]([N:25]=[CH:26][N:27]=4)[N:24]=3)[CH2:13][CH2:14]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53760718Methyl [6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-7-yl]carboxylate

Product 1

HCID 22989252[6-[3-[4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-7-yl]carboxylic acidYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.58 g of methyl [6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-7-yl]carboxylate was dissolved in 10 ml of ethanol; 8.0 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by stirring at room temperature for 1.5 hours. After cooling, the mixture was concentrated under reduced pressure. The residue was diluted with water and washed with ethyl acetate; 1N hydrochloric acid was added to adjust pH 4.5. The mixture was saturated with saline and extracted with tetrahydrofuran; the extract was dried over magnesium sulfate. The crystal obtained by concentration under reduced pressure was washed with ethyl ether, collected by filtration and dried to yield 788 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. washwashed with ethyl acetate
  5. addition1N hydrochloric acid was added
  6. extractionextracted with tetrahydrofuran
  7. dry with materialthe extract was dried over magnesium sulfate
  8. customThe crystal obtained by concentration under reduced pressure
  9. washwas washed with ethyl ether
  10. filtrationcollected by filtration
  11. customdried

Sources & evidence

ORD record
ord-bba2248a4b2549e5bd9d38dcb21f923c
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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