Hydrochloric Acid → [1,2,4]Triazolo[1,5-a]pyridin-2-amine, 8-(3,4-difluorophenyl)-6-fluoro-5,6,7,8-tetrahydro-

HRID 451463Notes

Reaction equation

HRID 451463 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[N:11]([N:16]=[C:17]([NH2:19])[N:18]=3)[CH:12]=[C:13]([F:15])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH:13]([F:15])[CH2:12][N:11]3[N:16]=[C:17]([NH2:19])[N:18]=[C:10]23)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67336806HCID 67336806, compound

Product 1

HCID 67342019[1,2,4]Triazolo[1,5-a]pyridin-2-amine, 8-(3,4-difluorophenyl)-6-fluoro-5,6,7,8-tetrahydro-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-(3,4-difluorophenyl)-6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (prepared in analogy to example 66a-c starting with 3-bromo-5-fluoropyridin-2-amine, 237 mg, 897 μmol) in ethanol (8 mL) and HCl (25% in water, 144 mg, 120 μL, 987 μmol) was hydrogenated at 80° C. and 80 bar for 18 hours in the presence of Pd/C (237 mg, 222 μmol). The catalyst was filtered off, washed thoroughly with MeOH and the solvents were evaporated. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane). The title compound was obtained as white foam (76 mg, 32%). MS ISP (m/e): 269.2 (100) [(M+H)+].

Workup

  1. customwas hydrogenated at 80° C.
  2. filtrationThe catalyst was filtered off
  3. washwashed thoroughly with MeOH
  4. customthe solvents were evaporated
  5. customThe crude material was purified by flash chromatography (silica gel, 50 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane)

Sources & evidence

ORD record
ord-899da1d616a141aea0523517674c68fe
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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