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

HRID 1727406노트

반응식

HRID 1727406 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a4c40f9c1e554c1aabd00e14bc71d177
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495110B2

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