HCID 178455798, compound → HCID 178420256, compound

HRID 271354Notes

Reaction equation

HRID 271354 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[CH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]3[N:23]=[CH:22][N:21]=[C:20]4[NH:24][N:25]=[CH:26][C:19]=34)[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([NH:17][C:18]3[N:23]=[CH:22][N:21]=[C:20]4[NH:24][N:25]=[CH:26][C:19]=34)[CH2:15][CH2:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 178455798HCID 178455798, compound

Product 1

HCID 178420256HCID 178420256, compoundYield 198.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.100 g of trans-[4-(4-phenyl-but-1-enyl)-cyclohexyl]-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine and 0.050 g of 10% palladium on carbon in 20 mL of ethanol was stirred under an atmosphere of hydrogen for 18 hours. The reaction was filtered to remove catalyst and concentrated under reduced pressure. Purification by C-18 reversed phase chromatography (0.1% trifluroacetic acid/water to 0.1% trifluoroacetic acid/acetonitrile) gave 0.200 g of pure product as a foam: HRMS=350.2324.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove catalyst
  3. concentrationconcentrated under reduced pressure
  4. customPurification by C-18

Sources & evidence

ORD record
ord-6f81de3d14a0474c86b898c0525ed164
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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