Pyridine → 5-(4-{2-[3-(1,1-Dioxido-2-isothiazolidinyl)phenyl]ethyl}-1-piperazinyl)-2-methylquinoline

HRID 15881

反応式

HRID 15881 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=3)[NH2:23])[CH2:14][CH2:13]2)[N:3]=1.Cl[CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31].N1C=CC=C[CH:35]=1>>[O:31]=[S:30]1(=[O:32])[CH2:29][CH2:28][CH2:35][N:23]1[C:22]1[CH:21]=[C:20]([CH2:19][CH2:18][N:15]2[CH2:14][CH2:13][N:12]([C:8]3[CH:7]=[CH:6][CH:5]=[C:4]4[C:9]=3[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]4)[CH2:17][CH2:16]2)[CH:26]=[CH:25][CH:24]=1

参加物

4

反応物 3

HCID 1049PyridineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

生成物 1

HCID 684273165-(4-{2-[3-(1,1-Dioxido-2-isothiazolidinyl)phenyl]ethyl}-1-piperazinyl)-2-methylquinoline

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline (D6, 30 mg) in pyridine (0.5 mL) was added 2-chloroethylsulfonyl chloride (13 μL). The mixture was stirred 1 h then concentrated in vacuo and partitioned between saturated aqueous sodium hydrogencarbonate solution and DCM. The organic layer was washed (water), dried (sodium sulfate) and concentrated in vacuo. The residue was dissolved in THF (1 mL) and cooled to 0° C. with stirring. To the stirred solution was added sodium hydride (60%, 20 mg). The mixture was warmed to room temperature and left to stand for 4 days. The reaction was diluted with water and concentrated in vacuo. The residue was partitioned between DCM and water. The organic layer was washed (water), dried (sodium sulfate) and concentrated in vacuo. The residue was purified by column chromatography (SiO2; EtOAc) to give the title compound (4.4 mg).

後処理

  1. concentrationthen concentrated in vacuo
  2. custompartitioned between saturated aqueous sodium hydrogencarbonate solution and DCM
  3. washThe organic layer was washed (water)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in THF (1 mL)
  7. stirringwith stirring
  8. additionTo the stirred solution was added sodium hydride (60%, 20 mg)
  9. temperatureThe mixture was warmed to room temperature
  10. waitleft
  11. waitto stand for 4 days
  12. additionThe reaction was diluted with water
  13. concentrationconcentrated in vacuo
  14. customThe residue was partitioned between DCM and water
  15. washThe organic layer was washed (water)
  16. dry with materialdried (sodium sulfate)
  17. concentrationconcentrated in vacuo
  18. customThe residue was purified by column chromatography (SiO2; EtOAc)

出典と根拠

ORDレコード
ord-80cddc9c8dd24184a7ce83db38a0b9d5
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

関連ノート

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