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Hydrochloric Acid → trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxy-N-benzenesulphonylcyclohexanecarboxamide

HRID 21896
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 21896
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([OH:20])=O)[N:4]=1.[C:21]1([S:27]([NH2:30])(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N12CCCN=C1CCCCC2.Cl>O1CCCC1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([NH:30][S:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:29])=[O:28])=[O:20])[N:6]=1
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15728507trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxycyclohexanecarboxylic acid

Produkt 1

HCID 15239633trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxy-N-benzenesulphonylcyclohexanecarboxamideAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxycyclohexanecarboxylic acid (1.0 g), prepared as in Example 11, in dry tetrahydrofuran (10 ml) was added dropwise to a stirred solution of 1,1-carbonyldiimidazole (0.57 g) in dry tetrahydrofuran (10 ml) under nitrogen. The reaction mixture was stirred 30 minutes at ambient temperature, heated to reflux for 30 minutes and cooled to ambient temperature. Benzenesulphonamide (0.56 g) was added followed by dropwise addition of 1,8-diazabicyclo (5.4.0) undec-7-ene (0.54) in dry tetrahydrofuran (5 ml). The reaction mixture was stirred for 24 hours at ambient temperature, refluxed for 6 hours then poured into 1N hydrochloric acid (80 ml) and extracted with 3×100 ml portions of diethyl ether. The combined ether extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica-gel, using a 2:1 dichloromethane/ethyl acetate eluant, to give 100 mg of the title compound, melting point 175° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. temperaturecooled to ambient temperature
  4. stirringThe reaction mixture was stirred for 24 hours at ambient temperature
  5. temperaturerefluxed for 6 hours
  6. extractionextracted with 3×100 ml portions of diethyl ether
  7. dry with materialThe combined ether extracts were dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was chromatographed on silica-gel

Quellen und Nachweise

ORD-Eintrag
ord-66998b7f00e74f96b7a19de6d7beba6e
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05426090

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