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

HRID 1804238ノート

反応式

HRID 1804238 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e04a65d5ac241ac8741f9828c3c81ed
出典データセット
uspto-grants-2013_01
特許番号
US08354401B2

反応ノート

読み込み中…