Pyridine → N-Cyclopropyl-N-{1-[2-(2-oxo-oxazolidin-3-yl)-benzoyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamide

HRID 1428962Notes

Reaction equation

HRID 1428962 reaction equation
[NH2:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH:26]2[CH2:28][CH2:27]2)[S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5].N1C=CC=CC=1.Cl[CH2:40][CH2:41][O:42][C:43](Cl)=[O:44]>C(Cl)(Cl)Cl.CCOC(C)=O>[CH:26]1([N:12]([CH:9]2[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C:3]3[CH:29]=[CH:30][CH:31]=[CH:32][C:2]=3[N:1]3[CH2:40][CH2:41][O:42][C:43]3=[O:44])[CH2:7][CH2:8]2)[S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 123052-Chloroethyl chloroformateHCID 24860819N-[1-(2-Amino-benzoyl)-piperidin-4-yl]-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 58002115N-Cyclopropyl-N-{1-[2-(2-oxo-oxazolidin-3-yl)-benzoyl]-piperidin-4-yl}-3-trifluoromethyl-benzenesulfonamideYield 83.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[1-(2-Amino-benzoyl)-piperidin-4-yl]-N-cyclopropyl-3-trifluoromethyl-benzenesulfonamide (11) (0.170 g, 0.34 mmol) and pyridine (0.035 g, 0.45 mmol) was taken up in 1 ml of CHCl3. Chloroformic acid 2-chloroethyl ester (0.049 g, 0.34 mmol) was added over 5 minutes, and stirred at room temperature for 2 h. The reaction mixture was diluted with 30 ml of EtOAc and washed with 10 ml of H2O. The organic layer was dried over MgSO4 and concentrated to dryness. The crude product was purified through a column of silica gel with a gradient of 70% to 100% EtOAc in hexane to afford the title compound 12 (colorless amorphous, 152 mg, 83%). LC: 100%. MS: m/z=537.

Workup

  1. washwashed with 10 ml of H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated to dryness
  4. customThe crude product was purified through a column of silica gel with a gradient of 70% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-37e08d77b8d24caeb2fa6728d38bb2f6
Source dataset
uspto-grants-2015_01
Patent number
US08937181B2

Reaction notes

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