Ammonium Hydroxide → 5-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione

HRID 2170142노트

반응식

HRID 2170142 반응식
C([O:3][C:4]([NH:6][N:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]1[C:18]([O:20]C)=O)=O)C.[OH-].[NH4+:23]>>[C:12]1([C:9]2[CH:10]=[CH:11][N:7]3[C:8]=2[C:18](=[O:20])[NH:23][C:4](=[O:3])[NH:6]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

3

반응물 2

HCID 14923Ammonium HydroxideHCID 90386155methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate

생성물 1

HCID 903861165-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione수율 38.1%

반응 조건

온도
110 °C

실험 절차

Methyl 1-((ethoxycarbonyl)amino)-3-phenyl-1H-pyrrole-2-carboxylate (1.00 g, 3.47 mmol) was taken in a pressure tube and ammonium hydroxide (30%, 67.5 mL, 1.73 mol) was added and sealed. The reaction mixture was stirred at 110° C. for 30 h and transferred to a round bottomed flask and concentrated under reduced pressure. Toluene was added to it and azeotroped to remove trace amount of water (3 times). Then residue obtained was triturated with ethyl acetate (50×2 mL) to afford 5-phenylpyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione (0.300 g, 38.1%). LCMS Condition B-39: retention time 1.49 min, [M+1]=228.0.

후처리

  1. customsealed
  2. customtransferred to a round bottomed flask
  3. concentrationconcentrated under reduced pressure
  4. additionToluene was added to it
  5. customazeotroped
  6. customto remove trace amount of water (3 times)
  7. customThen residue obtained
  8. customwas triturated with ethyl acetate (50×2 mL)

출처 및 근거

ORD 기록
ord-09ac7eee98a24cecbfeb1f9146261945
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050345B2

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