Piperidine → HCID 66655979, compound

HRID 1505472Notes

Reaction equation

HRID 1505472 reaction equation
N[C:2]1[C:3]2[C:27]3([CH2:31][CH2:30]OC3)[C:26](=[O:32])[NH:25][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)[N:7]=1.N1CCCC[CH2:34]1>CC(C)=O.C(OCC)(=O)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:6]2[N:7]=[CH:2][C:3]3[C:27](=[C:31]([CH3:34])[CH3:30])[C:26](=[O:32])[NH:25][C:4]=3[N:5]=2)=[N:9]1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 56598426HCID 56598426, compound

Product 1

HCID 66655979HCID 66655979, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg (1.388 mmol) of Example 4 were initially charged in acetone (50 ml), 0.274 ml (2.775 mmol) of piperidine was added and the mixture was heated under reflux for 1 h. After cooling, a precipitate was filtered off and washed with acetone, and the filtrate was concentrated under reduced pressure. This residue was then purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient). The material obtained in this manner was once more slurried in ethyl acetate, filtered off, washed with ethyl acetate and dried under high vacuum. This gave 101 mg of the title compound as a solid (18% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 h
  3. temperatureAfter cooling
  4. filtrationa precipitate was filtered off
  5. washwashed with acetone
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThis residue was then purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient)
  8. customThe material obtained in this manner
  9. filtrationfiltered off
  10. washwashed with ethyl acetate
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-8eebc0489ef9409e9a320a1e9fceff98
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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