1,8-Diazabicyclo(5.4.0)undec-7-ene → 9-Chloro-5-[1-(2-hydroxy-3-phenyl-propyl)-piperidin-3-yl]-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one

HRID 2212200노트

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HRID 2212200 반응식
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.N12CCCN=C1CCCCC2.[O:35]1[CH2:44][CH:36]1[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(O)C.C(O)(C)C.C(Cl)(Cl)Cl>[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH2:44][CH:36]([OH:35])[CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 948262-(Phenylmethyl)oxiraneHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

생성물 1

HCID 219637269-Chloro-5-[1-(2-hydroxy-3-phenyl-propyl)-piperidin-3-yl]-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one수율 84%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 21906603Chloroform isopropyl alcohol용매

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온도
60 °C

실험 절차

To a suspension of 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (100 mg, 0.22 mmol) in ethanol (5 mL) add 1,8-diazabicyclo[5.4.0]undec-7-ene (40 μL, 0.27 mmol). Stir the solution under nitrogen. To the solution add (2,3-epoxypropyl)-benzene and heat to approximately 60° C. and stir under nitrogen overnight. Concentrate the reaction and dissolve in 20% isopropanol/chloroform, wash with 1N HCl, 1N sodium thiosulfate, saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–1.5% methanol/chloroform) to give 85.0 mg of the title compound as a white solid, 84% yield. 1H NMR: consistent with structure. MS (ion spray) 452 (M+).

후처리

  1. stirringstir under nitrogen overnight
  2. concentrationConcentrate
  3. customthe reaction
  4. washwash with 1N HCl, 1N sodium thiosulfate, saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdry over magnesium sulfate
  6. concentrationconcentrate
  7. customPurify by flash chromatography on silica gel (eluting with 0–1.5% methanol/chloroform)

출처 및 근거

ORD 기록
ord-6152a8152b694533935296e7b7ee1b0b
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101891B2

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