1-Naphthalenesulfonyl chloride → HCID 11560264, compound

HRID 2219263Notes

Reaction equation

HRID 2219263 reaction equation
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][CH:22]=[C:21]2CCN(C)C.[CH2:30]([N:32]([CH:36](C)C)[CH:33](C)C)[CH3:31]>CN(C)C=O>[CH3:33][N:32]([CH3:36])[CH2:30][CH2:31][N:23]1[C:24]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[NH:15][S:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)(=[O:13])=[O:12])[CH:21]=[CH:22]1

Participants

5

Reactant 3

HCID 665601-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57438420HCID 57438420, compound

Product 1

HCID 11560264HCID 11560264, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

149.5 mg (0.66 mMol) of naphtalene-1-sulfonyl chloride were added to a solution of 122 mg (0.6 mMol) of 7-amino-3-(2-dimethylaminoethyl)-1H-indole in 2 ml of dimethylformamide and 116 mg of N-ethyldiisopropylamine. The reaction mixture was stirred at the room temperature for 20 hours. Then it was evaporated to dryness, slightly alkalinized with sodium bicarbonate solution and extracted with chloroform. The organic phase was repeatedly washed with water and saturated solution of sodium bicarbonate, it was separated and dried with anhydrous sodium sulfate. The organic solution was evaporated to dryness and the resulting solid was purified by chromatography, obtaining 120 mg (51%) of N-[1-(2-dimethylaminoethyl)-1H-indole-7-yl]-naphtalene-1-sulfonamide as a solid cream.

Workup

  1. customThen it was evaporated to dryness
  2. extractionextracted with chloroform
  3. washThe organic phase was repeatedly washed with water and saturated solution of sodium bicarbonate, it
  4. customwas separated
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe organic solution was evaporated to dryness
  7. customthe resulting solid was purified by chromatography

Sources & evidence

ORD record
ord-4c649c8f27624f438883c1121abce24e
Source dataset
uspto-grants-2008_08
Patent number
US07414070B2

Reaction notes

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