p-Toluenesulfonic acid monohydrate → Methyl (2,5-di oxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

HRID 551025노트

반응식

HRID 551025 반응식
[N+:1]([C:4]1[C:12]2[N:11]([CH2:13][C:14](OC)=[O:15])[C:10](=[O:18])[N:9]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.[Pd]>[O:18]=[C:10]1[N:11]2[CH2:13][C:14](=[O:15])[NH:1][C:4]3[CH:5]=[CH:6][CH:7]=[C:8]([C:12]=32)[N:9]1[CH2:19][C:20]([O:22][CH3:23])=[O:21]

참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66636623Dimethyl 2,2'-(4-nitro-2-oxo-1H-benzimidazole-1,3-diyl)diacetate

생성물 1

HCID 86629734Methyl (2,5-di oxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of dimethyl 2,2′-(4-nitro-2-oxo-1H-benzimidazole-1,3-diyl)diacetate from Step B (270 mg, 0.84 mmol) and 10% Pd/C (50 mg) in MeOH (100 mL) was stirred under an atmosphere of hydrogen (ca. 1 atm). After 2 h, the reaction was filtered through a Celite pad and concentrated in vacuo. The crude solid was dissolved in toluene (3 mL) and p-toluenesulfonic acid monohydrate (2 mg, 0.011 mmol) was added. The mixture was heated at reflux for 30 min and then concentrated in vacuo to give the title compound. MS: m/z=262 (M+1).

후처리

  1. filtrationthe reaction was filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude solid was dissolved in toluene (3 mL)
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 30 min
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-115af42059114480b545d35df31d2e4e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947677B2

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