4-Amino-1-Boc-piperidine → t-Butyl 4-[[5-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]piperidine-1-carboxylate

HRID 2080453Notes

Reaction equation

HRID 2080453 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][CH:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1>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][CH:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 23114584t-Butyl 4-[[5-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]piperidine-1-carboxylateYield 12.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1,4-dioxane (2.2 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (300 mg, 0.48 mmol) obtained in Example 54 and t-butyl 4-aminopiperidine-1-carboxylate (600 mg) was stirred at 120° C. for 5 days 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=3:1) to give the title compound (36 mg, 9%) 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=3:1)

Sources & evidence

ORD record
ord-1856eac99ce649c789264b8ab83607ca
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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