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Hydrochloric Acid → 8-(4-Fluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 451375
Notes
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Reaction equation

HRID 451375 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([N:14]=[C:15]([NH2:17])[N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.Cl>CCO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][N:10]3[N:14]=[C:15]([NH2:17])[N:16]=[C:9]23)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 673360828-(4-Fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 673367858-(4-Fluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8-(4-Fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (232 mg, 1.02 mmol) in EtOH (10 mL) and aqueous HCl solution (25%, 162 L, 1.12 mmol) was hydrogenated in the presence of palladium on charcoal (10%, 232 mg, 0.22 mmol) at 50 bar and 50° C. for 18 hours. The catalyst was filtered off, washed thoroughly with EtOH and the solvent was removed from the combined filtrates. Saturated aqueous NaHCO3 solution was added to the residue. The aqueous phase was extracted with CH2Cl2, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using dichloromethane/methanol (with 10% ammonia) as eluent. The title compound was obtained as a white solid (174 mg, 74%).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed thoroughly with EtOH
  3. customthe solvent was removed from the combined filtrates
  4. additionSaturated aqueous NaHCO3 solution was added to the residue
  5. extractionThe aqueous phase was extracted with CH2Cl2
  6. dry with materialthe combined organic phases were dried over sodium sulfate
  7. customthe solvent was evaporated
  8. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-87fbe42263864671b0594b6c301a0972
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486967B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes