N,N'-Dimethylethylenediamine → HCID 68553469, compound

HRID 1868094Notes

Reaction equation

HRID 1868094 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]1)(=[O:13])=[O:12].Br[C:22]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O.CCOC(C)=O.[Cu]I>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:22]2[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=2)[C:16](=[O:20])[CH2:15]1)(=[O:13])=[O:12]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 51938202-bromo-3-trifluoromethylpyridineHCID 8321444HCID 8321444, compound

Product 1

HCID 68553469HCID 68553469, compoundYield 3.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried microwave vial was charged with of 4-(naphthalene-2-sulfonyl)-piperazin-2-one (100 mg, 0.34 mmol), 2-bromo-3-trifluoromethyl pyridine (115.3 mg, 0.51 mmol), powdered anhydrous potassium carbonate (94 mg, 0.68 mmol), and CuI (6.5 mg, 0.034 mmol). The vial was purged and back-filled with N2. Anhydrous 1,4-dioxane (1.2 mL) was added, followed by 3.7 μL (0.034 mmol) of N,N′-dimethyl-1,2-ethylenediamine. The blue suspension was heated in a 110° C. oil bath for 48 hr. After cooling to room temperature, the brown suspension was diluted with H2O and EtOAc. The layers were separated, and the aqueous layer washed with EtOAc (2×). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by prep HPLC to provide 4.8 mg (3.2%) of 4-(Naphthalene-2-sulfonyl)-1-(3-trifluoromethyl-pyridin-2-yl)-piperazin-2-one as a light yellow solid.

Workup

  1. customThe vial was purged
  2. additionback-filled with N2
  3. additionAnhydrous 1,4-dioxane (1.2 mL) was added
  4. temperatureAfter cooling to room temperature
  5. customThe layers were separated
  6. washthe aqueous layer washed with EtOAc (2×)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-c9bdadf433cc40fd96245f68f5d1481f
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

Loading…