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Lawesson's reagent → HCID 58382116, 화합물

HRID 1628012
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HRID 1628012 반응식
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:24]=[C:23]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]([CH3:36])[CH:26]=3)[N:22]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:19]2=[N:20][CH:21]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:54])=CC=1>O1CCOCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12](=[S:54])[NH:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:24]=[C:23]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]([CH3:36])[CH:26]=3)[N:22]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:19]2=[N:20][CH:21]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 58382263HCID 58382263, 화합물

생성물 1

HCID 58382116HCID 58382116, 화합물수율 100.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

A flask was charged with 4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanamide (0.100 g, 0.157 mmol) and 1,4-dioxane (5 mL). Lawesson's Reagent (0.095 g, 0.235 mmol) was added and the mixture was stirred at about 85° C. for about 1 h. The mixture was cooled to rt, concentrated in vacuo and the residue was partitioned with EtOAc (10 mL) and saturated aqueous NaHCO3 (7 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanethioamide (0.103 g, 100%): LC/MS (Table 2, Method b) Rf=3.84 min; MS m/z 654 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customthe residue was partitioned with EtOAc (10 mL) and saturated aqueous NaHCO3 (7 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aa153369d44645bf8197b8addb8f3287
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785639B2

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