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Cesium carbonate → cis-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-tetrahydro-pyran-4-carbonitrile

HRID 1809110
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반응식

HRID 1809110 반응식
[N:1]1([C:11]([C:13]2[CH:14]=[C:15]([CH2:18][C:19]#[N:20])[S:16][CH:17]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.C(Cl)Cl>[N:1]1([C:11]([C:13]2[CH:14]=[C:15]([C:18]3([C:19]#[N:20])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[S:16][CH:17]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1
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반응물 3

HCID 10796Cesium carbonateHCID 21521Bis(2-bromoethyl) etherHCID 86646716cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile

생성물 1

HCID 86646717cis-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-tetrahydro-pyran-4-carbonitrile수율 32.8%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매
HCID 962Water용매
HCID 6344Dichloromethane용매

실험 절차

cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile (0.049 g, 0.17 mmol) and 1-bromo-2-(2-bromo-ethoxy)-ethane (0.04 g, 0.17 mmol) and caesium carbonate (1.0 mmol) in DMSO (2 mL) was stirred for 12 hr at room temperature. The mixture was diluted with water (5 mL) and DCM (5 mL). The organic layer was filtered and then evaporated to give an oil which was purified by HPLC eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.02 g). LCMS m/z 359.24 [M+H]+ RT=10.70 min (Analytical Method 2).

후처리

  1. filtrationThe organic layer was filtered
  2. customevaporated
  3. customto give an oil which
  4. customwas purified by HPLC
  5. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-d72f4e5fb04846bea7151a0e61ee5e1c
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362008B2

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