Cyclopropylamine → Methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate

HRID 1405527Notes

Reaction equation

HRID 1405527 reaction equation
Cl[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([NH2:25])[CH2:24][CH2:23]1>CS(C)=O>[CH:22]1([NH:25][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)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 77231183Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 67042136Methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Into a 20-mL sealed tube, was placed methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (200 mg, 0.67 mmol, 1.00 equiv), cyclopropanamine (10 mL), DMSO (1 mL). The resulting solution was stirred overnight at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with H2O. The resulting solids were collected by filtration and applied onto a silica gel column with PE/EA (50:1). This resulted in 182.4 mg (83%) of methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customInto a 20-mL sealed tube
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe resulting solution was diluted with H2O
  4. filtrationThe resulting solids were collected by filtration
  5. customThis resulted in 182.4 mg (83%) of methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-a1dcaca4d2734c46ab918500b2c92dcc
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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