Cesium carbonate → N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzamide

HRID 883680Notes

Reaction equation

HRID 883680 reaction equation
F[C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][NH:30][CH2:31][CH2:32][CH2:33][NH2:34].[C:35](=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:9]([N:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6](=[O:7])[C:5]1[CH:17]=[CH:18][C:2]([NH:34][CH2:33][CH2:32][CH2:31][N:30]([CH3:35])[CH2:29][CH2:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=2)=[C:3]([N+:19]([O-:21])=[O:20])[CH:4]=1)[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 20192832N~1~-[2-(Pyridin-2-yl)ethyl]propane-1,3-diamineHCID 607491584-fluoro-N,N-diisobutyl-3-nitrobenzamide

Product 1

HCID 69029055N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzamideYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-fluoro-N,N-diisobutyl-3-nitrobenzamide (2.07 g, 1 eq), N-(2-pyridin-2-ylethyl)propane-1,3-diamine (1.6 g, 1.2 eq) and cesium carbonate (4.5 g, 2 eq) in acetonitrile (70 ml) is heated under reflux for 3 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (100 ml) and water (40 ml). After decantation and extraction, the combined organic phases are washed with salt water, dried over Na2SO4 then evaporated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: dichloromethane 100 to dichloromethane/methanol 8:2) produces the expected compound in the form of a yellow oil (3.1 g; 92% yield).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthen concentrated under reduced pressure at 40° C
  4. extractionAfter decantation and extraction
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. customthen evaporated under reduced pressure at 40° C
  8. customPurification of the residue by flash chromatography on silica gel (eluent: dichloromethane 100 to dichloromethane/methanol 8:2)

Sources & evidence

ORD record
ord-7cba77d113594c7b963578ca3eb170d1
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Reaction notes

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