HCID 59278146, compound → HCID 59278390, compound

HRID 559638Notes

Reaction equation

HRID 559638 reaction equation
Br[C:2]1[CH:7]=[C:6]([C@@H:8]([NH:11][C:12]([C:14]2[C:15]3[CH:22]=[N:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[C:16]=3[CH:17]=[N:18][CH:19]=2)=[O:13])[CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[H][H]>[Pd].C(O)C.C(#N)C.O>[N:3]1[CH:2]=[CH:7][C:6]([C@@H:8]([NH:11][C:12]([C:14]2[C:15]3[CH:22]=[N:21][N:20]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)[C:16]=3[CH:17]=[N:18][CH:19]=2)=[O:13])[CH2:9][CH3:10])=[CH:5][CH:4]=1

Participants

7

Reactant 2

HCID 59278146HCID 59278146, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59278390HCID 59278390, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-1-(2-bromopyridin-4-yl)-propyl]-amide (165 mg, 0.363 mmol) and 10% palladium on carbon (77 mg) in ethanol (10 mL) was placed under 1 atmosphere of hydrogen (balloon). After 16 hours, diatamacous earth (300 mg) was added and the mixture and the solution was filtered through diatamacous earth and concentrated to afford an oil. The crude material was dissolved in a 4:1 mixture of acetonitrile in water and purified by reversed-phase HPLC. The desired fractions from the column were concentrated to remove the acetonitrile, diluted with saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated to afford the title compound.

Workup

  1. additiondiatamacous earth (300 mg) was added
  2. filtrationthe mixture and the solution was filtered through diatamacous earth
  3. concentrationconcentrated
  4. customto afford an oil
  5. custompurified by reversed-phase HPLC
  6. concentrationThe desired fractions from the column were concentrated
  7. customto remove the acetonitrile
  8. additiondiluted with saturated aqueous sodium bicarbonate
  9. extractionextracted with dichloromethane
  10. dry with materialThe organic phase was dried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ef9c0b0f21a34f09a3b10e4c25371764
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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