Isopropanol → 1-(3-((1-(Quinolin-2-YL)piperidin-4-YL)oxy)pyrazin-2-YL)piperidin-4-OL

HRID 454915노트

반응식

HRID 454915 반응식
Cl[C:2]1[C:3]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH:25]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+].C(O)(C)C>O>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[N:12]1[CH2:13][CH2:14][CH:9]([O:8][C:3]2[C:2]([N:25]3[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:10][CH2:11]1

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 585476872-(4-((3-Chloropyrazin-2-yl)oxy)piperidin-1-yl)quinoline

생성물 1

HCID 585478291-(3-((1-(Quinolin-2-YL)piperidin-4-YL)oxy)pyrazin-2-YL)piperidin-4-OL수율 17%

시약·촉매·용매 1

HCID 962Water용매

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온도
160 °C

실험 절차

To a mixture of 2-(4-((3-chloropyrazin-2-yl)oxy)piperidin-1-yl)quinoline (see PREPARATION P1.1; 0.1 g, 0.29 mmol) and piperidin-4-ol (0.029 g, 0.29 mmol) and K2CO3 (0.08 g, 0.58 mmol) was added isopropyl alcohol (i-PrOH) (2 mL) and water (0.5 ml). The solution was heated to 160° C. under microwave for 5 hours. Then the mixture was concentrated 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 60% EtOAc in petroleum ether) to give the title product (0.02 g, 0.04 mmol, 17% yield) as white solid. ESI-MS (M+1): 406 calc. for C23H27N5O2 405.

후처리

  1. concentrationThen the mixture was concentrated
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic extracts were washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-68a81750f9fb49929012f7b52d471e29
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497265B2

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