(3S)-3-methyl-1-pyridin-2-ylpiperazine → (S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403511Notes

Reaction equation

HRID 1403511 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:3]1.Cl[C:15]1[C:16](=[O:29])[NH:17][C:18]2[C:23]([N:24]=1)=[CH:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=2>CN1C(=O)CCC1>[CH3:1][C@H:2]1[CH2:3][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:5][CH2:6][N:7]1[C:15]1[C:16](=[O:29])[NH:17][C:18]2[C:23]([N:24]=1)=[CH:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=2

Participants

4

Reactant 2

HCID 1519492(3S)-3-methyl-1-pyridin-2-ylpiperazineHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 70665275(S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylateYield 67.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of (S)-3-methyl-1-(pyridin-2-yl)piperazine (748 mg, 4.22 mmol) in NMP (5 ml), was added methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1 g, 4.19 mmol). After stirring 1 h at 140° C., the resulting solution was quenched by the addition of water (100 ml) and filtered to give (S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (1.07 g, 67%).

Workup

  1. customthe resulting solution was quenched by the addition of water (100 ml)
  2. filtrationfiltered

Sources & evidence

ORD record
ord-fa45156a77ce4678ba3c216973c46fe3
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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