Trifluoromethanesulfonic anhydride → (S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

HRID 1403512ノート

反応式

HRID 1403512 の反応式
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:5][CH2:4][N:3]1[C:14]1[C:15](=[O:28])[NH:16][C:17]2[C:22]([N:23]=1)=[CH:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=2.[O:29](S(C(F)(F)F)(=O)=O)[S:30]([C:33]([F:36])([F:35])[F:34])(=O)=[O:31]>ClCCl>[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:5][CH2:4][N:3]1[C:14]1[C:15]([O:28][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:31])=[O:29])=[N:16][C:17]2[C:22]([N:23]=1)=[CH:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=2

参加物

4

反応物 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 70665275(S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

生成物 1

HCID 86670573(S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate収率 83.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (800 mg, 2.11 mmol) in dichloromethane (20 ml) under an inert atmosphere of nitrogen, was added TEA (958 mg, 9.47 mmol) followed by addition of Tf2O (1.19 g, 4.22 mmol) dropwise at −60° C. After stirring 5 min at this temperature, the reaction was quenched by the addition of water (100 ml), extracted with dichloromethane (2×30 ml), dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (2% ethyl acetate in petroleum ether) to afford (S)-methyl 3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red oil (0.9 g, 83.4%).

後処理

  1. customthe reaction was quenched by the addition of water (100 ml)
  2. extractionextracted with dichloromethane (2×30 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified via silica gel chromatography (2% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-6e15e92a86164790ad34f0bbc4009ccf
出典データセット
uspto-grants-2014_12
特許番号
US08912188B2

反応ノート

読み込み中…