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

HRID 2373653

Reaction equation

HRID 2373653 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-9da44bb58d6440c5a4f363a5c16a475f
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Linked notes

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