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

HRID 1727406ノート

反応式

HRID 1727406 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a4c40f9c1e554c1aabd00e14bc71d177
出典データセット
uspto-grants-2009_02
特許番号
US07495110B2

反応ノート

読み込み中…