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Acetyl chloride → cis-1-{4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanone

HRID 1809067
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HRID 1809067 반응식
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=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.N1CC[O:27][CH2:26][CH2:25]1.C(Cl)(=O)C>C(Cl)Cl>[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:19][CH2:20][N:21]([C:26](=[O:27])[CH3:25])[CH2:22][CH2:23]3)[S:15][CH:14]=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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8083MorpholineHCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone

생성물 1

HCID 86646703cis-1-{4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone [Enantiomer C] (CC-039) (0.150 g, 0.45 mmol) in DCM (2 mL) was added polymer supported morpholine (2.5 equivalents) and acetyl chloride (0.51 mmol). The reaction mixture was stirred for 3 hours, filtered and then the solvent evaporated. The product 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 (0.095 g). LCMS m/z 375.27 [M+H]+ RT=9.71 min (Analytical Method 2).

후처리

  1. filtrationfiltered
  2. customthe solvent evaporated
  3. customThe product was purified by HPLC
  4. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-41fbd67913ff42088274d2292e0de0b5
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362008B2

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