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Lawesson's reagent → 6-chloro-4'-[5-chloro-2-(1-methoxycarbamoyl-1-methyl-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-6'-thioxo spiro[3H-indole-3,3'-piperidine]-2(1H)-one

HRID 658950
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인쇄 미리보기

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HRID 658950 반응식
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27](=[O:31])[NH:28][O:29][CH3:30])([CH3:26])[CH3:25])[CH2:14][C:13](=O)[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:51])=CC=1>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27](=[O:31])[NH:28][O:29][CH3:30])([CH3:26])[CH3:25])[CH2:14][C:13](=[S:51])[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 87949Lawesson's reagentHCID 749287936-chloro-4'-[5-chloro-2-(1-methoxycarbamoyl-1-methyl-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl) spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

생성물 1

HCID 752934556-chloro-4'-[5-chloro-2-(1-methoxycarbamoyl-1-methyl-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-6'-thioxo spiro[3H-indole-3,3'-piperidine]-2(1H)-one수율 38.6%

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of racemic (2′S, 3S, 4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbamoyl-1-methyl-ethoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl) spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (25 mg, 0.042 mmol) and Lawesson's reagent (33 mg, 0.084 mmol) in THF (1 mL) was stirred at room temperature for 1 h, and then diluted with toluene (10 mL). The mixture was concentrated and the residue was washed with DCM twice. The DCM solutions were combined and concentrated. The residue was purified by flash column to give the title compound as white solid (10 mg).

후처리

  1. concentrationThe mixture was concentrated
  2. washthe residue was washed with DCM twice
  3. concentrationconcentrated
  4. customThe residue was purified by flash column

출처 및 근거

ORD 기록
ord-323943488b234673b2333b1e0f5d05e3
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08076482B2

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