Triethylamine → 1-{1-[3-(1-Quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanone

HRID 1850350

반응식

HRID 1850350 반응식
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH:22]1[CH2:27][CH2:26][CH:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]1.CCN(CC)CC>CS(C)=O.O>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[N:10]1[CH2:11][CH:8]([C:3]2[C:2]([N:22]3[CH2:27][CH2:26][CH:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27237641-(Piperidin-4-yl)ethan-1-oneHCID 585467412-(3-(3-Chloropyrazin-2-yl)azetidin-1-yl)quinoline

생성물 1

HCID 585472291-{1-[3-(1-Quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanone수율 63%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To a solution of 2-[3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-quinoline (80 mg, 0.27 mmol) and 1-piperidin-4-yl-ethanone (WUXI APPTEC) (34.3 mg, 0.27 mmol) in DMSO (5 mL) was added Et3N (54.5 mg, 0.54 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (20 mL×3). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel to give 1-{1-[3-(1-quinolin-2-yl-azetidin-3-yl)-pyrazin-2-yl]-piperidin-4-yl}-ethanone (65.8 mg, 0.17 mmol, yield 62.9%).

후처리

  1. extractionextracted with EtOAc (20 mL×3)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-5682078ac7aa4504a7b635e4daa2aa78
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957073B2

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