Methanol → HCID 10172811, compound

HRID 350701Notes

Reaction equation

HRID 350701 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH:15]([CH3:27])[CH2:16][NH:17][C:18]4[CH:23]=[N:22][N:21]([CH3:24])[C:20](=[O:25])[C:19]=4Cl)[CH2:11][CH2:10]3)=N[O:8][C:4]=2[CH:3]=1.C[OH:31].[OH-].[Na+].[H][H]>[Pd].O>[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]([CH3:27])[CH2:16][NH:17][C:18]3[CH:23]=[N:22][N:21]([CH3:24])[C:20](=[O:25])[CH:19]=3)[CH2:11][CH2:10]2)=[O:31])=[C:4]([OH:8])[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21088979HCID 21088979, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10172811HCID 10172811, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Into a pressure-tight hydrogenating apparatus 1.64 g (0.0039 mole) of 5-{2-[4-(6-fluoro-1,2-benzisoxazole-3-yl)-piperidine-1-yl]-propylamino}-4-chloro2-methyl-2H-pyridazine-3-one, 150 ml of a solvent mixture (9:1 mixture of methanol and distilled water), 0.18 g (0.0456 mole) of sodium hydroxide and 3.2 g of a palladium/charcoal catalyst (composition: 8% of palladium, 28% of carbon and 64% of water) are weighed in. The reaction mixture is stirred at a hydrogen pressure of 10 atm. for 24 hours. The reaction mixture is heated to reflux temperature and stirred at this temperature for 5 minutes. The mixture is filtered hot and the catalyst is washed five times with 33 ml of a 1:1 mixture of methanol and dichloro methane each. The united mother lyes are evaporated. The precipitated crude product is recrystallized from a mixture of acetonitrile and water. Thus 1.12 g of the desired compound are obtained. Yield 73.8%.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux temperature
  3. filtrationThe mixture is filtered hot
  4. washthe catalyst is washed five times
  5. additionwith 33 ml of a 1:1 mixture of methanol and dichloro methane each
  6. customThe united mother lyes are evaporated
  7. customThe precipitated crude product
  8. customis recrystallized from a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-df028d2e6ec9434bbfe0c307aeb75209
Source dataset
uspto-grants-2007_02
Patent number
US07183283B2

Reaction notes

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