Pyridine → 2-chloro-5-nitro-N-(4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}phenyl)benzamide

HRID 421558Notes

Reaction equation

HRID 421558 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].N1C=CC=CC=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][N:27]2[S:32]([C:35]2[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:21]=1.C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:39][C:38]1[CH:37]=[CH:36][C:35]([S:32]([N:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]2[C:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)(=[O:34])=[O:33])=[CH:41][CH:40]=1)=[O:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 117637Benzoyl chloride, 2-chloro-5-nitro-2×HCID 2770922{4-[(2-Pyridin-3-ylpiperidin-1-yl)sulfonyl]phenyl}amine

Product 1

HCID 35656982-chloro-5-nitro-N-(4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 220 mg portion of 2-chloro-5-nitrobenzoyl chloride was added to a pyridine solution (10 ml) of 318 mg of 4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}aniline and stirred overnight at room temperature. After stirring at 50° C. for 4 hours, 220 mg of 2-chloro-5-nitrobenzoyl chloride was further added thereto and stirred at 50° C. for 2 hours. Ethyl acetate and water were added thereto to carry out layer separation operation, and the organic layer was washed with saturated sodium chloride aqueous solution. After drying with anhydrous sodium sulfate, this was concentrated under a reduced pressure and the thus obtained residue was purified by a silica gel column chromatography using chloroform:methanol (98:2) as the elution solvent, thereby obtaining 426 mg of 2-chloro-5-nitro-N-(4-{[2-(pyridin-3-yl)piperidin-1-yl]sulfonyl}phenyl)benzamide as colorless crystals.

Workup

  1. stirringAfter stirring at 50° C. for 4 hours
  2. stirringstirred at 50° C. for 2 hours
  3. customlayer separation operation
  4. washthe organic layer was washed with saturated sodium chloride aqueous solution
  5. dry with materialAfter drying with anhydrous sodium sulfate
  6. concentrationthis was concentrated under a reduced pressure
  7. customthe thus obtained residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-f9f810c46e76467aa61a3fdee01759fa
Source dataset
uspto-grants-2012_01
Patent number
US08101580B2

Reaction notes

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