HCID 21106588, compound → HCID 21106581, compound

HRID 1783701Notes

Reaction equation

HRID 1783701 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 MeOH/THF 1:1 at RT. After completion of the reaction the catalyst was filtered off and the filtrate evaporated. The residue was dissolved in 50 ml DCM 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 DCM. 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 DCM
  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 DCM
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-fd6f54c7484f461ba2f808382012ecd5
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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