Aniline → HCID 11661462, compound

HRID 1765373Notes

Reaction equation

HRID 1765373 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:17]=[C:16]([NH:18][C:19]3[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:25])=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC([O-])(C)C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:24][C:22]1[NH:21][N:20]=[C:19]([NH:18][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:25])[N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:3][CH:4]=3)[N:17]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 11617275HCID 11617275, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 11661462HCID 11661462, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

2-(4-Chloro-phenyl)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one (B-1, 0.10 g, 0.28 mmol), aniline (0.034 g, 0.37 mmol), NaOtBu (0.041 g, 0.43 mmol), tris-(dibenzylideneacetone)-dipalladium (0.026 g, 0.028 mmol) and 2-(di-t-butylphosphino)-biphenyl (0.017 g, 0.057 mmol) under argon were heated to 100° C. for 17 hours, and then allowed to cool to room temperature. The solvent was evaporated in vacuum, the residue was diluted in H2O (50 ml) and the resulting solid was collected by filtration. Purification of the raw product by chromatography over silica gel with dichloromethane:MeOH (20:1) gave the title compound (0.002 g, 2% yield) as a white solid (example U-1). 1H-NMR: (400 MHz, D6-DMSO) 12.0 (1H, s), 9.23 (1H, s), 8.49 (1H, d), 8.33–8.37 (2H, m), 7.88–7.97 (2H, m), 7.54 (2H, d), 7.28 (2H, t), 7.15 (4H, m), 6.86 (1H, t), 6.25 (1H, s), 2.19 (3H, s); MS (API+)=409.0 (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuum
  2. additionthe residue was diluted in H2O (50 ml)
  3. filtrationthe resulting solid was collected by filtration
  4. customPurification of the raw product by chromatography over silica gel with dichloromethane:MeOH (20:1)

Sources & evidence

ORD record
ord-7a0a1f9e57f44b68b6fde9a92b086e4f
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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