Toluene → (S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

HRID 717038Notes

Reaction equation

HRID 717038 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8](=O)[NH:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2.C1(C)C=CC=CC=1.S(Cl)([Cl:31])=O>CN(C)C=O>[Cl:31][C:8]1[C:7]([N:3]2[CH2:4][CH2:5][CH2:6][C@@H:2]2[CH3:1])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 67041797(S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 86670565(S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (900 mg, 3.14 mmol, 1.00 equiv), toluene (20 mL), thionyl chloride (11.2 g, 94.12 mmol, 30.00 equiv), N,N-dimethylformamide (4 mL). The resulting solution was heated to reflux for 3 hr in an oil bath. The resulting mixture was concentrated under vacuum. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:50). This resulted in 143 mg (13%) of (S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 3 hr in an oil bath
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:50)
  6. customThis resulted in 143 mg (13%) of (S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as yellow oil

Sources & evidence

ORD record
ord-02c8a495ace14b70b4caf0d378ddef66
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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