Thiophenol → HCID 56651603, Verbindung

HRID 2369816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369816
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:24][C:25]2[C:34]3[C:29](=[C:30]([C:35]([NH2:37])=[O:36])[CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]([CH3:38])[N:26]=2)[CH2:9][N:10]([CH3:23])S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(S)C=CC=CC=1>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:24][C:25]2[C:34]3[C:29](=[C:30]([C:35]([NH2:37])=[O:36])[CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]([CH3:38])[N:26]=2)[CH2:9][NH:10][CH3:23])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 66714522HCID 66714522, Verbindung

Produkt 1

HCID 56651603HCID 56651603, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Crude 4-[((1S)-1-(4-Fluorophenyl)-2-{methyl[(4-nitrophenyl)sulfonyl]amino}ethyl)-amino]-2-methylquinazoline-8-carboxamide (161 mg; 0.30 mmol) and Cs2CO3 (488 mg; 1.50 mmol) were suspended in CH3CN (7 ml), and stirred for 10 minutes at room temperature. Benzenethiol (0.12 ml; 1.20 mmol) was added via syringe and the solution was stirred vigorously at room temperature overnight. The reaction mixture was concentrated, dissolved in DMSO (3 ml), and purified via Reverse Phase chromatography (Yamazen, basic buffer) to provide 9 16? (46 mg; 43% yield) as the free base. LC-MS [354 (M+1)]

Aufarbeitung

  1. stirringthe solution was stirred vigorously at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in DMSO (3 ml)
  4. custompurified via Reverse Phase chromatography (Yamazen, basic buffer)
  5. customto provide 9 16

Quellen und Nachweise

ORD-Eintrag
ord-d2903218fb8349ee8e15bb9c668d7ade
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710044B2

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