Trifluoroacetic acid → (4-Chloro-3-phenyl-2-(trifluoromethyl)quinolin-6-yl)(piperidin-4-yl)(pyridin-3-yl)methanol

HRID 1478528Notes

Reaction equation

HRID 1478528 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:32])([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[CH:10]=2)[N:5]=[C:4]([C:33]([F:36])([F:35])[F:34])[C:3]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[OH:32])[CH:10]=2)[N:5]=[C:4]([C:33]([F:35])([F:34])[F:36])[C:3]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118005527tert-Butyl 4-((4-chloro-3-phenyl-2-(trifluoromethyl)quinolin-6-yl)(hydroxy)(pyridin-3-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 118005518(4-Chloro-3-phenyl-2-(trifluoromethyl)quinolin-6-yl)(piperidin-4-yl)(pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-((4-chloro-3-phenyl-2-(trifluoromethyl)quinolin-6-yl)(hydroxy)(pyridin-3-yl)methyl)piperidine-1-carboxylate (313 mg, 0.520 mmol, Example 69) in DCM (6 mL) was treated with 1.8 mL of TFA, stirred for 3 hours, and concentrated. The residue was partitioned between saturated NaHCO3 aqueous solution and DCM. The organic layer was dried (Na2SO4), filtered and concentrated to dryness to provide the title compound as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.86 (s, 1H), 8.55 (s, 1H), 8.44 (d, J=4.55 Hz, 1H), 8.21 (d, J=9.09 Hz, 1H), 7.89-7.96 (m, 2H), 7.46-7.53 (m, 4H), 7.23-7.32 (m, 2H), 3.23-3.36 (m, 2H), 2.77-2.91 (m, 3H), 1.66-1.86 (m, 4H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between saturated NaHCO3 aqueous solution and DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3bc989bf3ec8474c924c763d70ab9883
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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