Trifluoroacetic acid → N-(3,3-difluoropiperidin-4-yl)-8-(2,3,4-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 451580Notes

Reaction equation

HRID 451580 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:32]=[C:18]3[C:19]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[C:24]=4[F:31])=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[C:10]([F:34])([F:33])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:34][C:10]1([F:33])[CH:11]([NH:14][C:15]2[N:32]=[C:18]3[C:19]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[C:24]=4[F:31])=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67342863HCID 67342863, compound

Product 1

HCID 67343436N-(3,3-difluoropiperidin-4-yl)-8-(2,3,4-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 3,3-difluoro-4-[8-(2,3,4-trifluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (110 mg, 228 μmol) in CH2Cl2 (4 mL) at 0° C. was added TFA (182 mg, 123 μl, 1.59 mmol) and stirred at room temperature for 18 hours. Further TFA (182 mg, 123 μl, 1.59 mmol) was added and stirred at 50° C. for 6 hours. The reaction mixture was extracted with saturated NaHCO3 solution and ethyl acetate, the organic layers combined, dried over Na2SO4, filtered and the solvents evaporated. The product was coevaporated four times with toluene. The title compound was obtained as light yellow foam (87 mg, 100%). MS ISP (m/e): 384.2 (100) [(M+H)+].

Workup

  1. stirringstirred at 50° C. for 6 hours
  2. extractionThe reaction mixture was extracted with saturated NaHCO3 solution and ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-687defbbbcfa4b1d9c94a87c6ff7be8e
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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