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Sodium Hydroxide → N-[(cis)-3-(5-fluoro-1H-indol-3-yl)cyclopentyl]-N-{[(2S)-8-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}amine

HRID 1824010
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인쇄 미리보기

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HRID 1824010 반응식
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[C@@H:35]1[CH2:39][CH2:38][C@H:37]([NH2:40])[CH2:36]1.[OH-].[Na+]>CS(C)=O>[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[C:29]2[C@@H:35]1[CH2:39][CH2:38][C@H:37]([NH:40][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)[CH2:36]1
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 11792133[(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonateHCID 68827169cis-3-(5-Fluoro-1H-indol-3-yl)-cyclopentylamine

생성물 1

HCID 10023651N-[(cis)-3-(5-fluoro-1H-indol-3-yl)cyclopentyl]-N-{[(2S)-8-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}amine수율 48%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

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온도
80 °C

실험 절차

A mixture of [(2R)-8-methoxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzene-sulfonate (0.5 g, 1.42 mmole) and cis-3-(5-fluoro-1H-indol-3-yl)-cyclopentyl-amine (0.24 g, 1.1 mmol) in anhydrous DMSO (10 mL) was heated at 80° C. for 30 h. The cooled reaction mixture was poured into 1 N aqueous NaOH (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), then were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 0.5 g of crude product. Flash chromatography on silica gel (10% MeOH/ethyl acetate) afforded 0.2 g (48%) of the title compound as a thick oil, which was converted to its hydrochloride salt (0.195 g): MS (ESI) m/z 397 [M+H]+.

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  4. dry with materialwere dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give 0.5 g of crude product

출처 및 근거

ORD 기록
ord-b7de644fc0da48e5973bdb107cbfc545
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07041697B2

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