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

HRID 1067571

Reaction equation

HRID 1067571 reaction equation
[C:1]1([CH:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([N:25]=[C:26]([C:28]([O:30]C(C)C)=[O:29])[N:27]=4)[N:24]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1>[C:34]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][O:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([N:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=4)[N:24]=3)[CH2:11][CH2:10]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53847838Isopropyl [6-[3-[4-(diphenylmethoxy) piperidino]propoxy][1,2,4]triazolo[1,5-b]pyridazin-2-yl]carboxylate

Product 1

HCID 22989225[6-[3-[4-(Diphenylmethoxy)piperidino]propoxy][1,2,4]triazolo[1,5-b]pyridazin-2-yl]carboxylic acidYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.85 g of isopropyl [6-[3-[4-(diphenylmethoxy) piperidino]propoxy][1,2,4]triazolo[1,5-b]pyridazin-2-yl]carboxylate was dissolved in 18 ml of tetrahydrofuran; 3.8 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by stirring at room temperature for 3.5 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was diluted with water and washed with ethyl acetate; 1 N hydrochloric acid was added to ajust pH 4.5. The mixture was crystallized by the addition of ethanol-acetone (1:2), collected by filtration, washed with water and ethyl acetate and dried to yield 1.33 g 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. addition1 N hydrochloric acid was added to ajust pH 4.5
  6. customThe mixture was crystallized by the addition of ethanol-acetone (1:2)
  7. filtrationcollected by filtration
  8. washwashed with water and ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-77bed7550a2240e09b3668918ce45c3c
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Linked notes

Loading…