2-Naphthalenesulfonyl chloride → HCID 70095056, compound

HRID 1532345Notes

Reaction equation

HRID 1532345 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].C([N:17](CC)CC)C.[CH3:22][N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]#[N:33])[CH:30]=2)[CH:25]=[C:24]1[CH2:34][CH2:35][C@@H:36]1[CH2:40][CH2:39][CH2:38][NH:37]1>ClCCl.O>[CH3:22][N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([NH2:17])=[NH:33])[CH:30]=2)[CH:25]=[C:24]1[CH2:34][CH2:35][C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[S:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 53937964HCID 53937964, compound

Product 1

HCID 70095056HCID 70095056, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a 25 ml flask, 30 mg of 1-methyl-2-((S)-2-pyrrolidin-2-ylethyl)indole-6-carbonitrile and 36 mg of 2-naphthalenesulfonyl chloride were dissolved in 3 ml of dichloromethane, and 0.055 ml of triethylamine was added at room temperature. The reaction mixture was stirred for 2 hours, diluted with water and then extracted three times with dichloromethane. The extracts were combined, dried over MgSO4 and then evaporated. The residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane (1:3)]. The fractions containing the pure desired product were combined and then evaporated to obtain 26.9 mg of the title compound as a pale yellow solid.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified with silica gel column chromatography [eluent: ethyl acetate/n-hexane (1:3)]
  5. additionThe fractions containing the pure desired product
  6. customevaporated

Sources & evidence

ORD record
ord-f72d6f46fb52480e894a3f84442dce80
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

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