Dimethylformamide → N'-[2-Methoxy-5-(5-methoxy-3-methyl indole-1-sulfonyl) phenyl]-N,N-dimethyl ethane-1,2-diamine

HRID 2425003Notes

Reaction equation

HRID 2425003 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[C:15]([CH3:24])=[CH:14]2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CN(C=O)C.Cl.[CH3:31][N:32]([CH3:36])[CH2:33][CH2:34]Cl>C1(C)C=CC=C(C)C=1>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[C:15]([CH3:24])=[CH:14]2)(=[O:11])=[O:12])=[CH:3][C:2]=1[NH:1][CH2:34][CH2:33][N:32]([CH3:36])[CH3:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 44603793HCID 44603793, compound

Product 1

HCID 25271510N'-[2-Methoxy-5-(5-methoxy-3-methyl indole-1-sulfonyl) phenyl]-N,N-dimethyl ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

1-(3′-Amino-4′-methoxy benzenesulfonyl)-5-methoxy-3-methyl-1H-indole (600 mg, 1.7 mmol) (obtained from preparation 2) was taken into a 25 mL two necked round bottom flask containing DMF (3 mL) and m-Xylene (3 mL). Added 2-dimethylamino ethyl chloride hydrochloride (490 mg, 3.4 mmol) and heated at 135° C.-138° C. for a period of 10 hours and the progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, the reaction mass was cooled to room temperature, quenched into chilled water (25 mL) and pH adjusted to 9.0 to 10.0 with 40% aqueous sodium hydroxide solution. The product was extracted with dichloromethane (2×50 mL). The organic layer was washed with brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain crude compound. The obtained technical product was purified by column chromatography, eluent being ethylacetate and triethylamine (99:1).

Workup

  1. customAfter completion of the reaction
  2. customquenched
  3. temperatureinto chilled water (25 mL)
  4. extractionThe product was extracted with dichloromethane (2×50 mL)
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain crude compound
  9. customThe obtained technical product was purified by column chromatography, eluent

Sources & evidence

ORD record
ord-720b4a18d62343f0b9d7c52246474860
Source dataset
uspto-grants-2011_06
Patent number
US07964627B2

Reaction notes

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