Diisopropylethylamine → 7-Fluoro-2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

HRID 734603Notes

Reaction equation

HRID 734603 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][C:15]([F:27])=[CH:16][C:17]=2[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[N:12]=1.CS(O[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=1)(=O)=O>CN(C)C=O>[F:27][C:15]1[CH:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([CH3:10])=[N:12]2)=[C:17]([N:21]2[CH2:26][CH2:25][N:24]([CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=3)[CH2:23][CH2:22]2)[CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 219738843-Nitrophenethyl methanesulfonateHCID 574443647-Fluoro-2-methyl-5-piperazin-1-ylquinoline

Product 1

HCID 574443667-Fluoro-2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinolineYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Diisopropylethylamine (0.07 mL; 3 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)-7-fluoro quinoline (0.03 g; 1 eq) and 2-(3-nitrophenyl)ethyl methanesulfonate (D4) (0.033 g; 1.1 eq) in dimethylformamide (1.0 mL). The reaction mixture was heated to 90° C. for 10 hours. The dark solution was cooled to room temperature and concentrated under reduced pressure, diluted with water (3 mL) and brine (1 mL) and extracted into ethyl acetate (3×3 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica, eluting with a gradient from dichloromethane to dichloromethane-MeOH (98:2) affording the title compound in 88% yield (0.04 g).

Workup

  1. temperatureThe dark solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water (3 mL) and brine (1 mL)
  4. extractionextracted into ethyl acetate (3×3 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by flash chromatography on silica
  8. washeluting with a gradient from dichloromethane to dichloromethane-MeOH (98:2)

Sources & evidence

ORD record
ord-7f7343f946a94a52a6b8d072e9ad2b6b
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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