Triethylamine → 5-[4-(1-Naphthalenesulfonylamino)butylthio]imidazo[1,2-a]pyridine

HRID 1081729Notes

Reaction equation

HRID 1081729 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:23]1([S:33](Cl)(=[O:35])=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:23]1([S:33]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)(=[O:35])=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 665601-Naphthalenesulfonyl chlorideHCID 233628945-[4-(Amino)butylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628855-[4-(1-Naphthalenesulfonylamino)butylthio]imidazo[1,2-a]pyridineYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (300 mg, 1.36 mmoles) and triethylamine (0.29 ml, 2.08 mmoles) in methylene chloride (15 ml) was added 1-naphthalenesulfonyl chloride (307 mg, 1.35 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent:ethyl acetate) to obtain 296 mg of the desired product (53.0%, colorless solid).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. washThe reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-4e8fad51db3a491a830a50793fe9b7a2
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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