1-(3-Aminopropyl)-2-pyrrolidinone → 1-[3-[[5-Chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]propyl]pyrrolidin-2-one

HRID 2080452Notes

Reaction equation

HRID 2080452 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]([S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])[C:5]([Cl:25])=[CH:4][N:3]=1.[NH2:26][CH2:27][CH2:28][CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][C:31]1=[O:35]>O1CCOCC1>[Cl:25][C:5]1[C:6]([CH:8]([S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])=[CH:7][C:2]([NH:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][C:31]2=[O:35])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 231147491-[3-[[5-Chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]propyl]pyrrolidin-2-oneYield 27%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1,4-dioxane (1.5 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (200 mg, 0.48 mmol) obtained in Example 54 and 1-(3-aminopropyl)pyrrolidin-2-one (400 μl) was stirred at 120° C. for 17 hours under an argon atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give the title compound (68 mg, 27%) as an oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5ba6ca7cabab451195906123a358405e
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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