N-BOC-ethylenediamine → HCID 23114557, compound

HRID 2080468Notes

Reaction equation

HRID 2080468 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.[C:26]([O:30][C:31](=[O:36])[NH:32][CH2:33][CH2:34][NH2:35])([CH3:29])([CH3:28])[CH3:27]>O1CCOCC1>[Cl:25][C:5]1[C:6]([CH:8]([S:17][C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])=[CH:7][C:2]([NH:35][CH2:34][CH2:33][NH:32][C:31](=[O:36])[O:30][C:26]([CH3:28])([CH3:27])[CH3:29])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 23114557HCID 23114557, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1,4-dioxane (6.0 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (610 mg, 1.46 mmol) obtained in Example 54 and t-butyl(2-aminoethyl)carbamate (700 mg, 4.38 mmol) was stirred at 120° C. for 4 days under an argon atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the title compound (176 mg, 22%) as an oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2bb00d33e83141beafb3273c3fc655a6
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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