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Lawesson's reagent → Ethyl 5-(7-[methyl(2-thienylsulfonyl)amino]-1h-indol-2-yl)-1,3,4-thiadiazole-2-carboxylate

HRID 1851524
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HRID 1851524 반응식
[CH3:1][N:2]([S:23]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)(=[O:25])=[O:24])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH:14][NH:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=O)=[CH:8]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>O1CCCC1>[CH3:1][N:2]([S:23]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)(=[O:24])=[O:25])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:40][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:15][N:14]=1)=[CH:8]2
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참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 59135607ethyl [2-({7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}carbonyl)hydrazino](oxo)acetate

생성물 1

HCID 136037568Ethyl 5-(7-[methyl(2-thienylsulfonyl)amino]-1h-indol-2-yl)-1,3,4-thiadiazole-2-carboxylate수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

A mixture of ethyl [2-({7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}carbonyl)hydrazino](oxo)acetate (0.43 g), Lawesson's reagent (0.42 g) and tetrahydrofuran (10 mL) was stirred at 50° C. overnight. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (0.29 g, yield 68%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 176-177° C.

후처리

  1. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-b9f57ea8362448119c0cc4ccdfbb0b8c
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957070B2

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