Triethylamine → 4-[2,5-Dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-3-methylsulfanyl-benzonitrile

HRID 59645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59645
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([C:21]1[C:26](=[O:27])[CH2:25][CH2:24][CH2:23][C:22]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[S:19][CH3:20].[C:39](N1C=CN=C1)(N1C=CN=C1)=[O:40]>C(#N)C>[O:40]=[C:39]1[NH:9][CH:10]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[S:19][CH3:20])[C:21]2[C:26](=[O:27])[CH2:25][CH2:24][CH2:23][C:22]=2[N:28]1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[CH:30]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 1186928904-{Amino-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-3-methylsulfanyl-benzonitrile hydrochloride2×

Produkt 1

HCID 1186929024-[2,5-Dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-3-methylsulfanyl-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Triethylamine (89 μL, 0.634 mmol) is added to a mixture of 4-{amino-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-3-methylsulfanyl-benzonitrile hydrochloride (INTERMEDIATE 5, 1.19 g, 2.54 mmol) and 1,1′-carbonyldiimidazole (480 mg, 2.96 mmol) in acetonitrile (4 mL) and the mixture is stirred at room temperature for 15 min. The reaction mixture is evaporated. Water is added, the precipitate is filtered and washed with water. The residue is dissolved in dichloromethane and evaporated. Yield: 1.02 g. ESI mass spectrum: [M+H]+=458; Retention time HPLC: 1.05 min (Z018_S04).

Aufarbeitung

  1. customThe reaction mixture is evaporated
  2. additionWater is added
  3. filtrationthe precipitate is filtered
  4. washwashed with water
  5. dissolutionThe residue is dissolved in dichloromethane
  6. customevaporated
  7. custom1.05 min (Z018_S04)

Quellen und Nachweise

ORD-Eintrag
ord-b63f83b7084342aab5e71bb433695c13
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440930B2

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