HCID 21106588, compound → HCID 21106581, compound

HRID 1765387Notes

Reaction equation

HRID 1765387 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:25][C:26]3[N:27]([C:32]([CH3:35])([CH3:34])[CH3:33])[N:28]=[C:29]([CH3:31])[CH:30]=3)=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)[C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO.C1COCC1>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:25][C:26]3[N:27]([C:32]([CH3:35])([CH3:34])[CH3:33])[N:28]=[C:29]([CH3:31])[CH:30]=3)=[N:9][N:10]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][CH:20]=3)[C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21106588HCID 21106588, compound

Product 1

HCID 21106581HCID 21106581, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2.00 g of 7-Nitro-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one were hydrogenated over palladium on charcoal in methanol/THF 1:1 at room temperature. After completion of the reaction the catalyst was filtered off and the filtrate evaporated. The residue was dissolved in 50 ml dichloromethane and extracted three times with a 3:1 mixture of water/conc. HCl. The combined aqueous phases were brought to pH 8 by addition of sodium bicarbonate and extracted with dichloromethane. Removal of the solvent yielded 1.25 g of the title product.

Workup

  1. customAfter completion of the reaction the catalyst
  2. filtrationwas filtered off
  3. customthe filtrate evaporated
  4. dissolutionThe residue was dissolved in 50 ml dichloromethane
  5. extractionextracted three times
  6. additionwith a 3:1 mixture of water/conc
  7. additionThe combined aqueous phases were brought to pH 8 by addition of sodium bicarbonate
  8. extractionextracted with dichloromethane
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-380b3a4aa6cf4332bd2d4007f2d30b7d
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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