Water → 4-(4-Bromo-2-methoxyphenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

HRID 517218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517218
CC(C)([O-])C.[Na+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:29]2[C:34](=O)[CH2:33][CH2:32][CH2:31][C:30]=2[O:36]CC)[NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)=[O:17])=[C:10]([O:39][CH3:40])[CH:9]=1.O>C(#N)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[C:29]3[C:30](=[O:36])[CH2:31][CH2:32][CH2:33][C:34]=3[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=3)[C:16](=[O:17])[NH:15]2)=[C:10]([O:39][CH3:40])[CH:9]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 867323361-((4-Bromo-2-methoxyphenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea2×

Produkt 1

HCID 867323374-(4-Bromo-2-methoxyphenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Sodium tert-butoxide (175 mg, 1.82 mmol) is added to a solution of 1-((4-bromo-2-methoxyphenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea (intermediate 49, 760 mg, 1.40 mmol) in acetonitrile (4 mL), and the mixture is shaked in an ultrasound bath for 20 min Water is added, and the mixture is extracted with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 41 mg; ESI mass spectrum [(79Br)-M+H]+=495, [(81Br)-M+H]+=497; Retention time HPLC: 0.96 min (Z011_S03).

Aufarbeitung

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  5. custom0.96 min (Z011_S03)

Quellen und Nachweise

ORD-Eintrag
ord-d792bca3a3514164a6ef4cfc0e4a7fac
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115093B2

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