N,N'-Dimethylethylenediamine → HCID 131735457, compound

HRID 632784Notes

Reaction equation

HRID 632784 reaction equation
I[C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]([CH3:10])[N:3]=1.[Si:11]([O:18][CH:19]1[C@H:23]([CH3:24])[NH:22][C:21](=[O:25])[C:20]1([CH3:27])[CH3:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COC1CCCC1.C(OCC)(=O)C.[Cu]I>[Si:11]([O:18][CH:19]1[C@H:23]([CH3:24])[N:22]([C:2]2[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]([CH3:10])[N:3]=2)[C:21](=[O:25])[C:20]1([CH3:26])[CH3:27])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 15264267HCID 15264267, compoundHCID 131735458HCID 131735458, compound

Product 1

HCID 131735457HCID 131735457, compoundYield 30.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 138539Cyclopentyl methyl etherSolvent

Procedure

A solution of 3-iodo-1-methyl-4-nitro-1H-pyrazole (197 mg), (5S)-4-((tert-butyl(dimethyl)silyl)oxy)-3,3,5-trimethylpyrrolidin-2-one (200 mg), copper(I) iodide (30 mg), N1,N2-dimethylethane-1,2-diamine (33 μL) and tripotassium phosphate (330 mg) in cyclopentyl methyl ether (5.0 mL) was stirred overnight at 120° C. The reaction mixture was diluted with ethyl acetate, the mixture was washed with saturated aqueous ammonium chloride solution, water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and then silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (90 mg).

Workup

  1. washthe mixture was washed with saturated aqueous ammonium chloride solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-305102b433fc4769b4236a990f6f6e22
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

Loading…