Ethanolamine → N-{6-[2-(5-Bromopyrimidin-2-yloxy)ethoxy]-2-(2-hydroxyethylamino)-5-(2-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

HRID 1599024

Reaktionsgleichung

Reaktionsgleichung von HRID 1599024
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[N:17]=[C:16](S(C)(=O)=O)[N:15]=[C:14]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:13]=2[O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[O:43][CH3:44])=[N:6][CH:7]=1.[CH2:45]([CH2:47][NH2:48])[OH:46].[Cl-].[NH4+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[N:17]=[C:16]([NH:48][CH2:47][CH2:45][OH:46])[N:15]=[C:14]([NH:22][S:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:30][CH:31]=3)(=[O:24])=[O:25])[C:13]=2[O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[O:43][CH3:44])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 25517Ammonium ChlorideHCID 10963585N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(2-methoxy-phenoxy)-2-methylsulfonylpyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

Produkt 1

HCID 18931063N-{6-[2-(5-Bromopyrimidin-2-yloxy)ethoxy]-2-(2-hydroxyethylamino)-5-(2-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamideAusbeute 11,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(2-methoxy-phenoxy)-2-methylsulfonylpyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (500 mg), ethanolamine (172 mg) and dimethylacetamide (4 ml) is heated with stirring at 110°-120° C. for 20 hours. After cooling, to the mixture is added an aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=3:1) to give the title compound (57 mg) as a powder.

Aufarbeitung

  1. temperatureis heated
  2. temperatureAfter cooling, to the mixture
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-8d2df527486946448fdc9890de0fd748
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739333

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