Pyridine → (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

HRID 1403622ノート

反応式

HRID 1403622 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[C:9](=[O:13])[NH:10]2)=[CH:5][C:4]=1[C:20]([O:22][CH3:23])=[O:21].N1C=CC=CC=1.[O:30](S(C(F)(F)F)(=O)=O)[S:31]([C:34]([F:37])([F:36])[F:35])(=O)=[O:32]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[C:9]([O:13][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:30])=[N:10]2)=[CH:5][C:4]=1[C:20]([O:22][CH3:23])=[O:21]

参加物

5

反応物 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70665330(S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

生成物 1

HCID 86670579(S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1.0 g, 3.15 mmol) in dichloromethane (80 ml) was added pyridine (990 mg, 12.52 mmol) and Tf2O (1.69 g, 5.99 mmol), and the reaction was stirred overnight under an atmosphere of nitrogen at room temperature. The reaction mixture was then quenched with water (200 ml), extracted with dichloromethane (3×30 mL), the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red oil (1.20 g, crude), which was used in the next step directly.

後処理

  1. customThe reaction mixture was then quenched with water (200 ml)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-05e187199bce40d19712e50bcda0dd6b
出典データセット
uspto-grants-2014_12
特許番号
US08912188B2

反応ノート

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