HCID 57504248, compound → HCID 57504330, compound

HRID 1097994Notes

Reaction equation

HRID 1097994 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([O:17][C@@H:18]([CH2:29][O:30][CH3:31])[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=3)=[O:20])=[C:11]2[CH:10]=[N:9]1>CO.[Pd]>[CH3:31][O:30][CH2:29][C@H:18]([O:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=3)[N:9]=[CH:10][C:11]=12)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=1)=[O:20]

Participants

4

Reactant 1

HCID 57504248HCID 57504248, compound

Product 1

HCID 57504330HCID 57504330, compoundYield 20.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium (10% on Carbon) (25.5 mg, 0.24 mmol) was added to (2S)-2-(1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-methoxy-N-(5-methylpyridin-2-yl)propanamide (Example 3) (105 mg, 0.24 mmol) in methanol (2.5 mL) at ambient temperature under nitrogen. This was then purged with hydrogen and the resulting solution was stirred at ambient temperature for 24 hours. The mixture was filtered through celite and evaporated. The residue was purified by flash silica chromatography eluting with 0 to 100% EtOAc in isohexane to afford (S)-3-methoxy-N-(5-methylpyridin-2-yl)-2-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide (20.0 mg, 20.7%).

Workup

  1. customThis was then purged with hydrogen
  2. filtrationThe mixture was filtered through celite
  3. customevaporated
  4. customThe residue was purified by flash silica chromatography
  5. washeluting with 0 to 100% EtOAc in isohexane

Sources & evidence

ORD record
ord-8a9833606b584efea34f119ebb968051
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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