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Dichloromethane → 5-(1-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidin-4-yl)piperidin-4-yl)-3-isopropyl-1,2,4-oxadiazole

HRID 1619438
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HRID 1619438 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20][CH2:19]3)=[CH:14][CH:13]=2)[N:5]=[CH:4][N:3]=1.Cl.[CH:27]([C:30]1[N:34]=[C:33]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[O:32][N:31]=1)([CH3:29])[CH3:28].ClCCl>>[CH3:24][C:21]1([CH3:25])[O:22][CH2:23][CH:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][C:6]3[N:5]=[CH:4][N:3]=[C:2]([N:38]4[CH2:37][CH2:36][CH:35]([C:33]5[O:32][N:31]=[C:30]([CH:27]([CH3:29])[CH3:28])[N:34]=5)[CH2:40][CH2:39]4)[C:7]=3[N+:8]([O-:10])=[O:9])=[CH:13][CH:14]=2)[CH2:19][O:20]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 534008274-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidine hydrochlorideHCID 866651624-Chloro-6-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidine

생성물 1

HCID 675155835-(1-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidin-4-yl)piperidin-4-yl)-3-isopropyl-1,2,4-oxadiazole수율 66%

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온도
27 °C

실험 절차

To an ice-cold solution of 4-chloro-6-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidine (500 mg, 0.0013 moles) and 3-isopropyl-5-(piperidin-4-yl)-1,2,4-oxadiazole hydrochloride (293 mg, 0.0015 mole) in dichloromethane (10 ml) diisopropyl ethyl amine (0.24 ml, 0.0016 mole) was added and the reaction mixture was stirred for 4 hours at 27° C. The reaction mixture was poured into ice cold water and extracted with dichloromethane. The organic extract was successively washed with water & brine, dried over calcium chloride and evaporated under reduced pressure. The crude product so obtained was purified by column chromatography using 20% ethyl acetate in hexane as eluent to yield 450 mg product as pale yellow solid.

후처리

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas successively washed with water & brine
  5. dry with materialdried over calcium chloride
  6. customevaporated under reduced pressure
  7. customThe crude product so obtained
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-25255abac72e45898cbf07f7411bd635
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772302B2

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