Hydrochloric Acid → 6-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine

HRID 1802186Notes

Reaction equation

HRID 1802186 reaction equation
[F:1][C:2]1[C:3]([NH:17]C(=O)OC(C)(C)C)=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[F:1][C:2]1[C:3]([NH2:17])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 67776795Tert-butyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate

Product 1

HCID 677751876-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amineYield 100%

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (252 mg, 767 μmol) and hydrochloric acid (5N in ether, 6 ml, 30.0 mmol) is stirred for 18 hours at 25° C. The mixture is adjusted to pH=ca 8 with sat. aqueous sodium carbonate solution and extracted twice with ethyl acetate, the organic layers are separated, dried with magnesium sulfate and the solvent is evaporated under reduced pressure affording 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (175 mg, 100%) as a light yellow solid. Mp.: >250° C. MS: m/z=229.2 (M+H+).

Workup

  1. extractionextracted twice with ethyl acetate
  2. customthe organic layers are separated
  3. dry with materialdried with magnesium sulfate
  4. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-4aa7feab727a4038bcd34f8d0321652a
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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