Cyclopentylamine → HCID 67042032, compound

HRID 717016Notes

Reaction equation

HRID 717016 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[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:22]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23]1>CCCCO>[CH:22]1([NH:27][C:2]2[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[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)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 67042032HCID 67042032, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Into an 8-mL sealed tube, was placed methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (200 mg, 0.58 mmol, 1.00 equiv), cyclopentanamine (246.8 mg, 2.90 mmol, 5.00 equiv), and n-BuOH (2 mL). The resulting solution was stirred for 4 hrs at 100° C. in an oil bath. The resulting mixture was concentrated in vacuo. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:50) resulting in 214.1 mg (crude) of methyl 3-(cyclopentylamino)-2-phenylquinoxaline-6-carboxylate as a yellow oil.

Workup

  1. customInto an 8-mL sealed tube
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:50)
  4. customresulting in 214.1 mg (crude) of methyl 3-(cyclopentylamino)-2-phenylquinoxaline-6-carboxylate as a yellow oil

Sources & evidence

ORD record
ord-50af1196b6624820bf665051bd0fe44e
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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