Pyridine → 6-Chloro-1-(4-methoxy-3-piperazin-1-ylbenzenesulfonyl)-5-methyl-2,3-dihydro-1H-indole hydrochloride

HRID 429149Notes

Reaction equation

HRID 429149 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][NH:14]2)=[CH:10][C:9]=1[CH3:17].ClC(Cl)(Cl)C([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([S:36](Cl)(=[O:38])=[O:37])[CH:31]=[CH:32][C:33]=2[O:34][CH3:35])[CH2:24][CH2:23]1)=O>ClCCl>[ClH:7].[Cl:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][N:14]2[S:36]([C:30]2[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:28]([N:25]3[CH2:26][CH2:27][NH:22][CH2:23][CH2:24]3)[CH:29]=2)(=[O:37])=[O:38])=[CH:10][C:9]=1[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11178065HCID 11178065, compoundHCID 221860806-Chloro-5-methyl-2,3-dihydro-1H-indole

Product 1

HCID 183545496-Chloro-1-(4-methoxy-3-piperazin-1-ylbenzenesulfonyl)-5-methyl-2,3-dihydro-1H-indole hydrochlorideYield 110.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.28 ml) was added to a stirred solution of 6-chloro-5-methyl-2,3-dihydro-1H-indole (WO-9501976) (0.116 g) and 3-(4-trichloroacetylpiperazin-1-yl)-4-methoxybenzenesulfonyl chloride (D4) (300 mg) in dichioromethane (4 ml) at room temperature. After 18 h the solution was washed with 1M hydrochloric acid (5 ml), water (5 ml), dried (MgSO4) and concentrated to an oil. The oil was dissolved in 1,4-dioxan (13 ml) and a 0.15 M potassium hydroxide solution (6.5 ml) was added. The solution was stirred at room temperature for 4 h then concentrated to remove the organic solvent, diluted with water (10 ml) and the solution extracted with dichloromethane (20 ml). The organic phase was dried (Na2SO4), acidified with 1M ethereal hydrogen chloride (2 ml), concentrated to a solid and stirred with acetone to afford the title compound (0.175 g, 55%). MH+ 422/424.

Workup

  1. washAfter 18 h the solution was washed with 1M hydrochloric acid (5 ml), water (5 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to an oil
  4. dissolutionThe oil was dissolved in 1,4-dioxan (13 ml)
  5. additiona 0.15 M potassium hydroxide solution (6.5 ml) was added
  6. concentrationthen concentrated
  7. customto remove the organic solvent
  8. additiondiluted with water (10 ml)
  9. extractionthe solution extracted with dichloromethane (20 ml)
  10. dry with materialThe organic phase was dried (Na2SO4)
  11. concentrationconcentrated to a solid
  12. stirringstirred with acetone

Sources & evidence

ORD record
ord-8e0f5063581d4fe9b011a3ff69a13f43
Source dataset
uspto-grants-2001_11
Patent number
US06316450B1

Reaction notes

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