Trifluoroacetic acid → 5-(4-Chloro-phenyl)-6-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridin-3-ylamine

HRID 1958147Notes

Reaction equation

HRID 1958147 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([NH:28]C(=O)OC(C)(C)C)[CH:18]=[N:19][C:20]=2[O:21][C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24])=[CH:11][CH:10]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[C:17]([NH2:28])[CH:18]=[N:19][C:20]=2[O:21][C@@H:22]([CH3:27])[C:23]([F:24])([F:25])[F:26])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67281043(S)-tert-butyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-3-ylcarbamate

Product 1

HCID 672815945-(4-Chloro-phenyl)-6-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridin-3-ylamineYield 82.7%

Procedure

Trifluoroacetic acid (2.74 g, 1.85 ml, 24.0 mmol) was added to (S)-tert-butyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-3-ylcarbamate (0.350 g, 840 μmol). The resulting yellow solution was stirred at RT for 1 h. The solvent was evaporated. The residue was partitioned between ethyl acetate and 1M Na2CO3 solution, the organic phase was dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 5 to 50% EtOAc in heptane) to give 0.22 g (82%) of the title compound as light brown oil; MS (EI) 317.1 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customThe residue was partitioned between ethyl acetate and 1M Na2CO3 solution
  3. dry with materialthe organic phase was dried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 20 g, 5 to 50% EtOAc in heptane)

Sources & evidence

ORD record
ord-0312189baf22477fa40e0f2e4f556d52
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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