Dimethylformamide → HCID 68870367, compound

HRID 734552Notes

Reaction equation

HRID 734552 reaction equation
[CH:1]([N:4]([CH2:8][CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])C.C[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([F:27])[CH:15]=CC=2N2CCNCC2)[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.C[N:45](C)C=O>>[F:27][C:14]1[C:13]([CH3:18])=[N:12][C:11]2[C:7]([CH:15]=1)=[C:5]([N:4]1[CH2:8][CH2:9][N:45]([CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=3)[CH2:3][CH2:1]1)[CH:6]=[CH:19][CH:20]=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 219738843-Nitrophenethyl methanesulfonateHCID 574443218-Fluoro-2-methyl-5-piperazin-1-yl-quinoline

Product 1

HCID 68870367HCID 68870367, compoundYield 46%

Conditions

Temperature
100 °C

Procedure

N,N-Diisopropylethylamine (0.25 mL; 3 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)-8-fluoro quinoline (0.170 g; 1 eq) and 2-(3-nitrophenyl)ethyl methanesulfonate (D4) (0.17 g; 1 eq) in dimethylformamide (4.0 mL). The reaction mixture was heated to 100° C. for 10 hours. The dark solution was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water (3 mL) and brine (1 mL) and extracted into ethyl acetate (3×3 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with a gradient from dichloromethane to dichloromethane-methanol (98:2) affording the title compound in 46% yield (0.126 g).

Workup

  1. temperatureThe dark solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water (3 mL) and brine (1 mL)
  4. extractionextracted into ethyl acetate (3×3 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by flash chromatography on silica gel
  8. washeluting with a gradient from dichloromethane to dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-d783dbfdd39048edae11066fd87e0c1d
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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