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Sodium hydride → 1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-1-(1-methanesulfonyl-1H-pyrazol-3-yl)-propyl]-amide

HRID 1698161
Notes
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Reaction equation

HRID 1698161 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C@@H:6]([NH:9][C:10]([C:12]2[C:13]3[CH:20]=[N:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:14]=3[CH:15]=[N:16][CH:17]=2)=[O:11])[CH2:7][CH3:8])=[N:2]1.[H-].[Na+].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C1COCC1>[CH3:30][S:31]([N:1]1[CH:5]=[CH:4][C:3]([C@@H:6]([NH:9][C:10]([C:12]2[C:13]3[CH:20]=[N:19][N:18]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[C:14]=3[CH:15]=[N:16][CH:17]=2)=[O:11])[CH2:7][CH3:8])=[N:2]1)(=[O:33])=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 1784560771-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(1H-pyrazol-3-yl)-propyl]-amide

Product 1

HCID 592781571-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-1-(1-methanesulfonyl-1H-pyrazol-3-yl)-propyl]-amide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a room temperature solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(1H-pyrazol-3-yl)-propyl]amide (0.040 g, 0.11 mmol) in THF was added 60% sodium hydride (9 mg, 0.2 mmol) in mineral oil. After 20 minutes, methansulfonyl chloride (25 mg, 0.22 mmol) was added. After 3 hours, the reaction was quenched with saturated aqueous ammonium chloride and the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (the column was equilibrated with dichloromethane-Et3N) eluting with 5% methanol in dichloromethane. Material from the column was crystallized in ether to afford the title compound.

Workup

  1. waitAfter 3 hours
  2. customthe reaction was quenched with saturated aqueous ammonium chloride
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (the column
  8. washeluting with 5% methanol in dichloromethane
  9. customMaterial from the column was crystallized in ether

Sources & evidence

ORD record
ord-884dfaba77d345778fc54c3ba0804f51
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163918B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes