5-[1-(Methylsulfonyl)-4-piperidyloxy]-3-nitroimidazo[1,2-a]pyridine → 3-Amino-5-[1-(methylsulfonyl)-4-piperidyloxy]imidazo[1,2-a]pyridine

HRID 1081748Notes

Reaction equation

HRID 1081748 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[N:17]3[C:18]([N+:21]([O-])=O)=[CH:19][N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]>C(Cl)Cl.[H][H].[C].[Pd]>[NH2:21][C:18]1[N:17]2[C:12]([O:11][CH:8]3[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][CH2:7]3)=[CH:13][CH:14]=[CH:15][C:16]2=[N:20][CH:19]=1

Participants

5

Reactant 1

HCID 233629815-[1-(Methylsulfonyl)-4-piperidyloxy]-3-nitroimidazo[1,2-a]pyridine

Product 1

HCID 233629073-Amino-5-[1-(methylsulfonyl)-4-piperidyloxy]imidazo[1,2-a]pyridineYield 132.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution of 5-[1-(methylsulfonyl)-4-piperidyloxy]-3-nitroimidazo[1,2-a]pyridine (70 mg, 0.226 mmole) in methylene chloride (10 ml) was added 10% palladium-carbon (50 ml) and the mixture was stirred in hydrogen atmosphere at room temperature for 1.5 hours. After the reaction mixture was treated with Cellite, the solvent was distilled off. To the residue was added chloroform, which was washed in turn with an aqueous saturated 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:chloroform/methanol (15:1)] to obtain 93 mg of the desired product (30.0%, brown oily product).

Workup

  1. additionAfter the reaction mixture was treated with Cellite
  2. distillationthe solvent was distilled off
  3. additionTo the residue was added chloroform, which
  4. washwas washed in turn with an aqueous saturated sodium bicarbonate solution and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography [eluent:chloroform/methanol (15:1)]

Sources & evidence

ORD record
ord-75165a87994d41babee1adb05896e3a5
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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