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Trifluoroacetic acid → [6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

HRID 494001
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HRID 494001 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([N:23]3[CH2:28][CH2:27][S:26](=[O:30])(=[O:29])[CH2:25][CH2:24]3)=[O:22])[N:8]2[CH2:11][CH2:12][O:13][Si](C(C)(C)C)(C)C)=[CH:4][C:3]=1[O:31][CH:32]1[CH2:37][CH2:36][N:35]([CH:38]([CH3:40])[CH3:39])[CH2:34][CH2:33]1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([N:23]3[CH2:24][CH2:25][S:26](=[O:30])(=[O:29])[CH2:27][CH2:28]3)=[O:22])[N:8]2[CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[O:31][CH:32]1[CH2:37][CH2:36][N:35]([CH:38]([CH3:40])[CH3:39])[CH2:34][CH2:33]1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67073382[6-Bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone

생성물 1

HCID 16739676[6-Bromo-1-(2-hydroxy-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone수율 99%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

A mixture of [6-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-methanone (130 mg, 1.0 eq.) and trifluoroacetic acid in dichloromethane was stirred for 1 h at room temperature and concentrated in vacuo. The crude mixture was partitioned between an aqueous solution of sodium hydroxide and dichloromethane. The aqueous layer was extracted with dichloromethane. Combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo, to yield 106 mg (99%) of the desired product as white foam. MS (m/e): 542.1 (M+H, 100%).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe crude mixture was partitioned between an aqueous solution of sodium hydroxide and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-38778f87b7d6432bb6e252e01981ab38
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07538101B2

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