Water → HCID 10225814, compound

HRID 271049Notes

Reaction equation

HRID 271049 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][S:16]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)(=[O:18])=[O:17])[CH:13]=2)[NH:8][CH:7]=1)[CH3:2].[CH3:31][C:32](C)([O-])C.[K+].C(I)C.O>CS(C)=O>[CH2:29]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N:15]([CH2:31][CH3:32])[S:16]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)(=[O:17])=[O:18])[CH:13]=2)[NH:8][CH:7]=1)[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 10202396N-[3-[2-(diethylamino)ethyl]-1H-indol-5-yl]naphthalene-2-sulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 10225814HCID 10225814, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 285 mg (0.7 mMol) of N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]naphthalene-2-sulphonamide (example 17) and 80 mg (0,7 mMol) of potassium t-butoxide in 3 ml of DMSO are stirred for 30 minutes at ambient temperature. Then are added 105 mg (0.7 mMol) of ethyl iodide and left with stirring for 3 hours. Water is added and is extracted with ethyl acetate. The organic solution is evaporated to dryness and the resulting crude is purified by chromatography on silica gel, using as an eluent mixtures of methylene chloride/methanol/ammonia, yielding N-[3-(2-diethylaminoethyl)-1H-indol-5-yl]-N-ethyl-naphthalene-2-sulphonamide as a solid with m.p. 49-50° C.

Workup

  1. waitleft
  2. stirringwith stirring for 3 hours
  3. extractionis extracted with ethyl acetate
  4. customThe organic solution is evaporated to dryness
  5. customthe resulting crude is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1b47462330304cf38ae05a9f5ec604b0
Source dataset
uspto-grants-2008_11
Patent number
US07452881B2

Reaction notes

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