Trifluoroacetic acid → HCID 118005805, compound

HRID 1507306Notes

Reaction equation

HRID 1507306 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([OH:26])[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]([O:27][CH3:28])[C:3]=1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[OH:26])[CH:10]=2)[N:5]=[C:4]([O:27][CH3:28])[C:3]=1[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([F:38])([F:37])[F:39])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 14798Sodium HydroxideHCID 118005850HCID 118005850, compound

Product 1

HCID 118005805HCID 118005805, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-((4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(hydroxy)methyl)piperidine-1-carboxylate (110 mg, 0.19 mmol, Intermediate 11: step a) in DCM (5 mL) was added TFA (75 μL, 0.97 mmol). The resulting solution was stirred at room temperature for 2 hours. TFA (75 μL, 0.97 mmol) was added and the mixture stirred at room temperature overnight. Then the reaction was diluted with DCM, cooled to 0° C., and the pH adjusted to ˜pH 8 by the addition of 3 N aqueous NaOH dropwise. The layers were separated and the organics dried (MgSO4), filtered and concentrated to dryness to afford the title compound which was used without further purification.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. temperaturecooled to 0° C.
  3. customThe layers were separated
  4. dry with materialthe organics dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-67bbd1ec809446999e21b9fbc6049b88
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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