Dimethyl Sulfoxide → (1H-benzoimidazol-2-yl)-{3-[3-(4-hydroxy-piperidin-1-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone

HRID 1850334노트

반응식

HRID 1850334 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:21](Cl)=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:13]1)=[O:11].[NH:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1.C(N(CC)CC)C.CS(C)=O>O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:21]([N:23]3[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]3)=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:13]1)=[O:11]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 58546731(1H-benzoimidazol-2-yl)-[3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-methanone

생성물 1

HCID 58547358(1H-benzoimidazol-2-yl)-{3-[3-(4-hydroxy-piperidin-1-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone수율 85%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

To a mixture of (1H-benzoimidazol-2-yl)-[3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-methanone (0.170 g, 0.50 mmol) and piperidin-4-ol (0.101 g, 1.0 mmol) was added triethylamine (0.10 g, 1.0 mmol) and DMSO (4 mL). The solution was heated to 120° C. for 4 h. Then the mixture was diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in petroleum ether) to give (1H-benzoimidazol-2-yl)-{3-[3-(4-hydroxy-piperidin-1-yl)-pyrazin-2-yl]-azetidin-1-yl}-methanone (0.16 g, 0.42 mmol, 85% yield) as a white solid.

후처리

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts were washed with water (10 mL) and brine (10 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 (20% to 50% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-89389f856d074c97beb1384e87f9cbe0
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957073B2

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