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Lawesson's reagent → HCID 58010138, 화합물

HRID 2204621
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HRID 2204621 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][C:23](=O)C3C=CC=CC=3)[N:20]=[C:15]2[CH:14]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[C:16]2[N:17]=[CH:18][C:19]3[N:20]([CH:23]=[N:22][CH:21]=3)[C:15]=2[CH:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 87949Lawesson's reagentHCID 58010182HCID 58010182, 화합물

생성물 1

HCID 58010138HCID 58010138, 화합물수율 56.4%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

N-((6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)benzamide (0.118 g, 0.218 mmol) in 1,4-dioxane (3 mL) was treated with Lawesson's Reagent (0.070 g, 0.17 mmol) and was heated to about 80° C. in an oil bath for about 20 min. The mixture was cooled to ambient temperature and then mercuric acetate (0.073 g, 0.23 mmol) was added. The mixture was stirred for about 60 min at ambient temperature then another portion of mercuric acetate (0.069 g, 0.22 mmol) was added and stirring was continued for about 20 min at ambient temperature. The mixture was diluted with EtOAc (20 mL) and then filtered. The filtrate was concentrated under reduced pressure and the material was purified by silica gel chromatography eluting with EtOAc to give 7-(5-methoxy-1-methyl-1H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.055 g, 48%): LC/MS (Table 2, Method d) Rt=1.91 min; MS m/z: 524 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringstirring
  3. waitwas continued for about 20 min at ambient temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe material was purified by silica gel chromatography
  7. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-308d8e0bd00144de86673a4731353341
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365579B2

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