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

HRID 1179634노트

반응식

HRID 1179634 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6885fa77dce94e1a85d75dfb98d5e404
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279481B2

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