Water → HCID 58532846, compound

HRID 906629Notes

Reaction equation

HRID 906629 reaction equation
C(OC([N:6]1[CH:11](OCC)[CH2:10][CH:9](Cl)[C:8]([C:16]2[CH:21]=[C:20]([C:22]([O:24]C)=[O:23])[C:19]([NH:26]C(=O)C)=[CH:18][C:17]=2[C:30]([F:33])([F:32])[F:31])=[N:7]1)=O)C.[OH-].[K+].O>CCO>[NH2:26][C:19]1[CH:18]=[C:17]([C:30]([F:31])([F:32])[F:33])[C:16]([C:8]2[N:7]=[N:6][CH:11]=[CH:10][CH:9]=2)=[CH:21][C:20]=1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 58532855HCID 58532855, compound

Product 1

HCID 58532846HCID 58532846, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 3-(4-acetylamino-5-methoxycarbonyl-2-trifluoromethyl-phenyl)-4-chloro-6-ethoxy-5,6-dihydro-4H-pyridazine-1-carboxylic acid ethyl ester (400 mg, 0.81 mmol) in EtOH (20 mL) containing KOH (227 mg, 4.05 mmol) was heated to 110° C. for 18 h. Water (2 mL) was added and the reaction was heated to 110° C. for 8 h. The solution was poured onto ice/water/2 N aq HCl (2.5 mL) then extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4) and the solvent was removed in vacuo to give the title compound (170 mg, 74%). API-ES: m/z 284.0 [M+H]+, rt 2.78 min.

Workup

  1. temperaturethe reaction was heated to 110° C. for 8 h
  2. additionThe solution was poured onto ice/water/2 N aq HCl (2.5 mL)
  3. extractionthen extracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-980d6da63cee42ecbddf570ab8d56ab2
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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