Diisopropylethylamine → HCID 16340978, compound

HRID 2365395Notes

Reaction equation

HRID 2365395 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=1.CCN(C(C)C)C(C)C>C(#N)C>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 231360Piperazin-2-one

Product 1

HCID 16340978HCID 16340978, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperazinone (1.16 g, 11.6 mmol), 2-chloro-5-(trifluoromethyl)pyridine (2.10 g, 11.6 mmol) and i-Pr2NEt (4.6 g, 6.4 mL, 36 mmol) were heated at reflux for 40 h in acetonitrile (60 mL). The mixture was concentrated, and the residue was purified by column chromatography (40 g ISCO column eluting with methylene chloride and a 10:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 90% methylene chloride) to provide the title compound (370 mg, 13%) as a yellow powder: ESI MS m/z 246 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography (40 g ISCO column
  3. washeluting with methylene chloride

Sources & evidence

ORD record
ord-5fe21e75b6334d7292d5b885a6eef7e9
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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