Hydrochloric Acid → 8-(4-Fluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine
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]=1Participants
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
- filtrationThe catalyst was filtered off
- washwashed thoroughly with EtOH
- customthe solvent was removed from the combined filtrates
- additionSaturated aqueous NaHCO3 solution was added to the residue
- extractionThe aqueous phase was extracted with CH2Cl2
- dry with materialthe combined organic phases were dried over sodium sulfate
- customthe solvent was evaporated
- customthe residue purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-87fbe42263864671b0594b6c301a0972
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486967B2
Reaction notes
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