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

HRID 1608612Notes

Reaction equation

HRID 1608612 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.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([NH: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)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 233628945-[4-(Amino)butylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628625-[4-(Methanesulfonamido)butylthio]imidazo[1,2-a]pyridineYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (440 mg, 1.99 mmoles) and triethylamine (0.42 ml, 3.01 mmoles) in methylene chloride (20 ml) was added methanesulfonyl chloride (0.19 ml, 2.45 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture was washed in turn with an aqueous saturated sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 302 mg of the desired product (50.8%, light red brown solid).

Workup

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

Sources & evidence

ORD record
ord-755b670acf204a89a5eb6ca5f3036de5
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

Loading…