Hydrochloric Acid → HCID 70155602, compound

HRID 276937Notes

Reaction equation

HRID 276937 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]3[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:20][N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=34)=[N:12]2)[C:7](=[O:33])[CH2:6]1)=[O:4].[OH-].[Na+].Cl>CO>[C:3]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]3[C:19]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[N:20][N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=34)=[N:12]2)[C:7](=[O:33])[CH2:6]1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70156042HCID 70156042, compound

Product 1

HCID 70155602HCID 70155602, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of cis-3-[2-(4-methoxycarbonyl-2-oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (80 mg) and 1N aqueous sodium hydroxide (2 ml) in methanol (4 ml) was heated at 50° C. for 4 hours. The solution was acidified with 1N aqueous hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with diethyl ether to give cis-3-[2-(4-carboxy-2-oxocyclohexyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (57 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-701348a7f271486fa4fa21800e8de67a
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Reaction notes

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