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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1619438
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
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Komponenten

4

Edukt 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

Produkt 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-oxadiazoleAusbeute 66 %

Reaktionsbedingungen

Temperatur
27 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-25255abac72e45898cbf07f7411bd635
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772302B2

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