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

HRID 1403527노트

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HRID 1403527 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 887Methanol용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6bb684154dc74ebfa1aa56846bac0f9e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912188B2

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