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Lawesson's reagent → HCID 69016906, 화합물

HRID 1854467
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HRID 1854467 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C)[CH:7]=[C:6]2[C:13]1[N:25]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][CH:23]=O)[N:20]=[C:15]2[CH:14]=1.[CH3:34]OC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1([CH3:34])[CH:11]=[CH:10][C:9]2[C:5]([C:6]([C:13]3[N:25]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:31])[CH3:32])[C:16]4[N:17]=[CH:18][C:19]5[N:20]([CH:23]=[N:22][CH:21]=5)[C:15]=4[CH:14]=3)=[CH:7][N:8]=2)=[CH:4]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 87949Lawesson's reagentHCID 58010272HCID 58010272, 화합물

생성물 1

HCID 69016906HCID 69016906, 화합물수율 82.5%

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)formamide (0.10 g, 0.22 mmol) in 1,4-dioxane (4 mL) was treated with Lawesson's Reagent (0.053 g, 0.13 mmol) and heated to about 80° C. in an oil bath for about 15 min. The mixture was cooled and mercuric acetate (0.073 g, 0.23 mmol, Fluka) was added. The mixture was stirred for about 30 min at ambient temperature and another portion of mercuric acetate (0.073 g, 0.228 mmol, Fluka) was added and stirring was continued for about 2 h at ambient temperature. The mixture was diluted with EtOAc (20 mL) and filtered. The solvent was evaporated under reduced pressure then the material was purified by silica gel chromatography eluting with DCM/MeOH (95:5). The material obtained after concentration of the product-containing fractions was further purified by silica gel chromatography eluting with EtOAc to give 7-(5-methoxy-5-methyl-5H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.048 g, 49%): LC/MS (Table 2, Method a) Rt=3.16 min; MS m/z: 448 (M+H)+.

후처리

  1. temperatureThe mixture was cooled
  2. stirringstirring
  3. waitwas continued for about 2 h at ambient temperature
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe material was purified by silica gel chromatography
  7. washeluting with DCM/MeOH (95:5)
  8. customThe material obtained after concentration of the product-containing fractions
  9. customwas further purified by silica gel chromatography
  10. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-8f66db087bde42cb94f99959dce09f72
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962629B2

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