Piperidine → HCID 11856040, compound

HRID 1162916Notes

Reaction equation

HRID 1162916 reaction equation
CS(O[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[C:18]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[NH:19][C:20]3=[O:23])=[CH:15][CH:14]=2)[CH2:8]1)(=O)=O.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>C(#N)C>[O:12]=[C:10]1[N:9]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[C:18]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:31])([F:33])[F:32])[NH:19][C:20]3=[O:23])=[CH:15][CH:14]=2)[CH2:8][C@H:7]([CH2:6][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[O:11]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 57558146HCID 57558146, compound

Product 1

HCID 11856040HCID 11856040, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The methanesulfonic acid (R)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl(20 mg, 0.0415 mmol) obtained in step A was dissolved in acetonitrile (0.1 ml). Thereafter, piperidine (8.2 μl) was added to the solution, and the obtained mixture was stirred under heating to reflux for 12 hours. Thereafter, the reaction solution was concentrated, and the obtained residue was then purified by silica gel column chromatography (methylene chloride:methanol=30:1), so as to obtain 7-((S)-2-oxo-5-piperidin-1-ylmethyloxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (14.3 mg, 73%) in the form of a colorless amorphous substance.

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 12 hours
  3. concentrationThereafter, the reaction solution was concentrated
  4. customthe obtained residue was then purified by silica gel column chromatography (methylene chloride:methanol=30:1)

Sources & evidence

ORD record
ord-6ebb1c3d34d34f82a5aeaffd1f144c70
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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