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

HRID 397564Notes

Reaction equation

HRID 397564 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:25]([C:28]([O:30]CC)=[O:29])=[N: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:33]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:25]([C:28]([OH:30])=[O:29])=[N:26][N:27]=4)[N:24]=3)[CH2:11][CH2:10]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23000327Ethyl 6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate

Product 1

HCID 230003206-[3-[4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazine-3-carboxylic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.31 g of ethyl 6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate was dissolved in 8 ml of ethanol; 8 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by refluxing under heating for 3 hours. After cooling, the ethanol was distilled off; the residue was washed with ethyl acetate; 1 N hydrochloric acid was added to reach pH 5. The precipitated crystal was collected by filtration, washed with water and ethyl acetate, and dried, to yield 1.19 g of the title compound.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling
  4. distillationthe ethanol was distilled off
  5. washthe residue was washed with ethyl acetate
  6. addition1 N hydrochloric acid was added
  7. filtrationThe precipitated crystal was collected by filtration
  8. washwashed with water and ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-94f94c9e4ae848be912962217945f889
Source dataset
uspto-grants-2003_08
Patent number
US06610694B1

Reaction notes

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