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

HRID 1850350

反応式

HRID 1850350 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5682078ac7aa4504a7b635e4daa2aa78
出典データセット
uspto-grants-2015_02
特許番号
US08957073B2

関連ノート

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