Ammonium Chloride → (S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

HRID 1403527ノート

反応式

HRID 1403527 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:14]=3)[N:9]=2)=[CH:4][C:3]=1[N+:28]([O-])=O.[NH4+].[Cl-]>CO.[Fe]>[NH2:28][C:3]1[CH:4]=[C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:14]=3)[N:9]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 70664899(S)-methyl 2-(4-amino-3-nitrophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

生成物 1

HCID 70664863(S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of (S)-methyl 2-(4-amino-3-nitrophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (1.0 g, 2.45 mmol) in methanol (40 mL) was added Fe (1.38 g, 24.6 mmol) and NH4Cl (1.3 g, 24.30 mmol). After the resulting solution was stirred for 6 h at 60° C., the solids were filtered out. The filtrate was concentrated under vacuum and dissolved in water (200 mL), extracted with dichloromethane (3×80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford (S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as yellow solid (970 mg, crude).

後処理

  1. filtrationthe solids were filtered out
  2. concentrationThe filtrate was concentrated under vacuum
  3. dissolutiondissolved in water (200 mL)
  4. extractionextracted with dichloromethane (3×80 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-6bb684154dc74ebfa1aa56846bac0f9e
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…