Tetrahydrofuran → 3-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxo-isothiazolidin-2-yl)phenyl}oxazolidin-2-one

HRID 1804238Notes

Reaction equation

HRID 1804238 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:24]2[CH2:28][CH2:27][O:26][C:25]2=[O:29])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=2)[CH2:12][CH2:11]1)=[O:9].C(N(CC)CC)C.O1CCCC1.Cl[CH2:43][CH2:44][CH2:45][S:46](Cl)(=[O:48])=[O:47]>O>[CH3:22][C:21]1[C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:24]4[CH2:28][CH2:27][O:26][C:25]4=[O:29])=[CH:3][C:2]=3[N:1]3[CH2:43][CH2:44][CH2:45][S:46]3(=[O:48])=[O:47])=[O:9])[CH2:15][CH2:14]2)=[N:17][CH:18]=[C:19]([CH3:23])[CH:20]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 673810033-{3-Amino-4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

Product 1

HCID 461902283-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(1,1-dioxo-isothiazolidin-2-yl)phenyl}oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-{3-amino-4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one (93.1 mg) described in Example 133, triethylamine (63 μL) and tetrahydrofuran (1 mL) was added 3-chloropropanesulfonyl chloride (38 μL), and the mixture was stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. To the residue were added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (42 μL) and DMF (1 mL), and the mixture was stirred at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. To the residue was added a mixed solvent of isopropyl ether and ethyl acetate, and the precipitated crystals were collected by filtration to give the title compound (62.1 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. additionTo the residue were added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (42 μL) and DMF (1 mL)
  5. stirringthe mixture was stirred at room temperature
  6. additionWater was added to the reaction mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. customthe solvent was evaporated
  10. additionTo the residue was added a mixed solvent of isopropyl ether and ethyl acetate
  11. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-1e04a65d5ac241ac8741f9828c3c81ed
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

Loading…