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N,N'-Dimethylethylenediamine → 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-methanesulfonyl-pyridin-3-yl)-cyclopropyl]-amide

HRID 2172978
Notes
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Reaction equation

HRID 2172978 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:30][S:31]([O-:33])=[O:32].[Na+].CNCCNC.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C.[I+].[Cu+]>[CH3:30][S:31]([C:2]1[N:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)(=[O:33])=[O:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 25517Ammonium ChlorideHCID 2733271Sodium methanesulfinateHCID 529167991-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide

Product 1

HCID 529168001-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-methanesulfonyl-pyridin-3-yl)-cyclopropyl]-amide

Reagents, catalysts & solvents 3

HCID 178505377HCID 178505377, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
130 °C

Procedure

A solution of 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide (72.7 mg, 0.161 mmol), sodium methanesulfinate (32.8 mg, 0.321 mmol) and copper (I) iodine (61.2 mg, 0.321 mmol) in DMSO (1 mL) is evacuated and purged with argon three times and heated at 130° C. After 45 minutes, the reaction is cooled to room temperature and N,N′-dimethylethylenediamine (69 μL, 0.64 mmol) is added. The mixture is stirred for 30 minutes, diluted with ethyl acetate (20 mL) and stirred for 15 minutes. A saturated aqueous solution of ammonium chloride (20 mL) is added; the resulting mixture is sonicated for 30 minutes, and diluted with ethyl acetate (100 mL). Phases are separated and the aqueous layer is extracted with ethyl acetate (3×20 mL). The combined organic layers are washed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated. The resulting residue is purified by silica gel chromatography eluting with a gradient of 0-8% methanol in methylene chloride to afford the title compound as a solid.

Workup

  1. custompurged with argon three times
  2. temperaturethe reaction is cooled to room temperature
  3. stirringstirred for 15 minutes
  4. customthe resulting mixture is sonicated for 30 minutes
  5. customPhases are separated
  6. extractionthe aqueous layer is extracted with ethyl acetate (3×20 mL)
  7. washThe combined organic layers are washed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue is purified by silica gel chromatography
  12. washeluting with a gradient of 0-8% methanol in methylene chloride

Sources & evidence

ORD record
ord-950ce9b8c8d845dbbebad6346a89ab8b
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056858B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes