Piperidine → HCID 86683052, compound

HRID 1497231Notes

Reaction equation

HRID 1497231 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[C:7](OS(C(F)(F)F)(=O)=O)[C:6]([C:21]#[N:22])=[C:5]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[C:7]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:6]([C:21]#[N:22])=[C:5]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 86683051HCID 86683051, compound

Product 1

HCID 86683052HCID 86683052, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 6-chloro-3-cyano-8-fluoro-4-phenyl-quinolin-2-yl ester (189 mg, 0.439 mmol), piperidine (150 mg, 174 μl, 1.76 mmol) and potassium carbonate (121 mg, 0.878 mmol) in THF (6 ml) was heated to 70° C. for 60 min. The yellow suspension was cooled to room temperature, diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was triturated with dichloromethane and the off-white solid was filtered off. The filtrate was evaporated and the remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-95:5) to afford the title compound (60 mg, 37%) as yellow solid. MS (ESI): 366.4 (M+H)+.

Workup

  1. temperatureThe yellow suspension was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe remaining residue was triturated with dichloromethane
  7. filtrationthe off-white solid was filtered off
  8. customThe filtrate was evaporated
  9. customthe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-95:5)

Sources & evidence

ORD record
ord-8410288b7c514566b4355b43e773bc3c
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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