3-amino-5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridine → Hydrochloric Acid

HRID 2213073Notes

Reaction equation

HRID 2213073 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]([Cl:11])=[O:10])[CH2:5][CH2:4]1.[F:12][C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[C:20]1[CH:21]=[C:22]2[C:28]([NH2:29])=[N:27][NH:26][C:23]2=[CH:24][N:25]=1>N1C=CC=CC=1>[ClH:11].[ClH:1].[F:12][C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[C:20]1[CH:21]=[C:22]2[C:28]([NH:29][C:9]([CH:6]3[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]3)=[O:10])=[N:27][NH:26][C:23]2=[CH:24][N:25]=1

Participants

5

Reactant 2

HCID 219482673-amino-5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridineHCID 219565061-Methylpiperidine-4-carbonyl chloride hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 865918741-Methyl4-piperidinecarboxylic acid [5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl]amide hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Methyl-4-piperidinecarbonyl chloride hydrochloride (400 mg, 2.02 mmol) was added to a solution of 5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridin-3-ylamine (100 mg, 0.41 mmol) in pyridine (4.5 mL). The reaction mixture was stirred at reflux for 48 hours, allowed to cool and concentrated. Purification by column chromatography using 20% v/v of a 2M methanolic ammonia solution in chloroform as eluent, and subsequent treatment of the product with 1M hydrogen chloride in ether afforded the title compound as a solid.

Workup

  1. temperatureat reflux for 48 hours
  2. temperatureto cool
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-37b30b8ff23c46faa9786963013df89f
Source dataset
uspto-grants-2006_09
Patent number
US07105532B2

Reaction notes

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