Cesium carbonate → 5-(4-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

HRID 1619441

반응식

HRID 1619441 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([O:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[O:25][N:24]=[C:23]([CH:26]([CH3:28])[CH3:27])[N:22]=3)[CH2:17][CH2:16]2)[C:9]=1[CH3:29].[CH3:30][C:31]1([CH3:44])[O:36][CH2:35][CH:34]([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[CH2:33][O:32]1>CN(C=O)C>[CH3:30][C:31]1([CH3:44])[O:32][CH2:33][CH:34]([C:37]2[CH:42]=[CH:41][C:40]([O:43][C:8]3[N:13]=[CH:12][N:11]=[C:10]([O:14][CH:15]4[CH2:20][CH2:19][N:18]([C:21]5[O:25][N:24]=[C:23]([CH:26]([CH3:28])[CH3:27])[N:22]=5)[CH2:17][CH2:16]4)[C:9]=3[CH3:29])=[CH:39][CH:38]=2)[CH2:35][O:36]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 675102564-(2,2-Dimethyl-1,3-dioxan-5-yl)phenolHCID 865973665-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

생성물 1

HCID 675159055-(4-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole수율 44.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Cesium carbonate (755 mg, 0.002317 moles) was added to a solution of 5-(4-(6-chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole (1.2 gm, 0.003365 moles) and 4-(2,2-dimethyl-1,3-dioxan-5-yl)phenol (700 mg, 0.003365 moles) in dry DMF (10 ml) and the reaction mixture was stirred at 80° C. for 3 hours. Then reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product so obtained was purified by column chromatography (silica gel) using 15% ethyl acetate in hexane as eluent to obtain 770 mg product as white solid.

후처리

  1. customThen reaction mixture
  2. additionwas poured into ice cold water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas successively washed with water & brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product so obtained
  9. customwas purified by column chromatography (silica gel)

출처 및 근거

ORD 기록
ord-8547c1dc5c5647e9843dc3f5e033f4f9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772302B2

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