Cesium carbonate → (1-{3-[1-(6-Methyl-quinolin-2-yl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-4-yl)-methanol

HRID 1850353노트

반응식

HRID 1850353 반응식
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:7]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]3)=[N:8][CH:9]=[CH:10][N:11]=2)[CH2:3]1.Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH3:31])[CH:27]=2)[N:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:31][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([N:2]1[CH2:5][CH:4]([C:6]3[C:7]([N:12]4[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]4)=[N:8][CH:9]=[CH:10][N:11]=3)[CH2:3]1)[CH:30]=[CH:29]2

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 779742-Chloro-6-methylquinolineHCID 67469292[1-(3-Azetidin-3-YL-pyrazin-2-YL)-piperidin-4-YL]-methanol hydrochloride

생성물 1

HCID 58546745(1-{3-[1-(6-Methyl-quinolin-2-yl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-4-yl)-methanol수율 26%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of [1-(3-azetidin-3-yl-pyrazin-2-yl)-piperidin-4-yl]-methanol hydrochloride (284 mg, 1.0 mmol) and 2-chloro-6-methyl-quinoline (purchased from ALDRICH) (177 mg, 1.0 mmol) in DMF (15 mL) was added Cs2CO3 (650 mg, 2.0 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography (EtOAc:Petrol ether=5:1) on silica gel to give (1-{3-[1-(6-methyl-quinolin-2-yl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-4-yl)-methanol (102 mg, 0.26 mmol 26%).

후처리

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic extracts were washed with water (20 mL) and brine (20 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 (EtOAc:Petrol ether=5:1) on silica gel

출처 및 근거

ORD 기록
ord-9b52aa63cb45416cadc6129f3d96df0a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957073B2

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