Cyclopentylamine → HCID 70664643, compound

HRID 1403631Notes

Reaction equation

HRID 1403631 reaction equation
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1>CS(C)=O.O>[CH:23]1([NH:28][C:2]2[C:3]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 2906CyclopentylamineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70664643HCID 70664643, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (250 mg, 0.79 mmol) in DMSO (3 mL) was added cyclopentylamine (402.6 mg, 4.73 mmol), and the resulting solution was stirred overnight at 100° C. The resulting mixture was diluted with water (15 mL) and extracted with dichloromethane (3×10 mL), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (2%-5% ethyl acetate in petroleum ether) to afford methyl 3-(cyclopentylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (240 mg, 69%).

Workup

  1. extractionextracted with dichloromethane (3×10 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified via silica gel column chromatography (2%-5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-34697a4b7d644ab8afe9c70e73e6802f
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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