Morpholine → 7-(5-morpholin-4-ylmethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162905Notes

Reaction equation

HRID 1162905 reaction equation
CS(O[CH2:6][CH: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][O:37][CH2:36][CH2:35]1>C(#N)C>[N:34]1([CH2:6][CH:7]2[O:11][C:10](=[O:12])[N:9]([C:13]3[CH:22]=[C:21]4[C:16]([CH:17]=[C:18]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:32])([F:31])[F:33])[NH:19][C:20]4=[O:23])=[CH:15][CH:14]=3)[CH2:8]2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 575578752-Oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl methanesulfonate

Product 1

HCID 118544507-(5-morpholin-4-ylmethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl methanesulfonate (20.0 mg, 0.0415 mmol) obtained in step C of Example 1-30 was dissolved in acetonitrile (0.1 ml). Thereafter, morpholine (3.6 μl) was added to the obtained solution, and the obtained mixture was stirred under heating to reflux for 22 hours. Thereafter, the reaction solution was cooled to a room temperature, and it was then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1), so as to obtain 7-(5-morpholin-4-ylmethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (9.7 mg; yield: 49%) in the form of a colorless amorphous substance.

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 22 hours
  3. concentrationit was then concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1)

Sources & evidence

ORD record
ord-1dcfd1dce16e452595cf6fdd4c8cfe70
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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