Pyridine → n-{4-Chloro-2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}(2-fluoro-4-cyanophenyl)carboxamide

HRID 12171

Reaktionsgleichung

Reaktionsgleichung von HRID 12171
[F:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=1)=[O:22].N1C=CC=CC=1>S(Cl)(Cl)=O.ClCCl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:4]([C:3]2[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][C:2]=2[F:1])=[O:6])=[C:15]([C:21](=[O:22])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)[CH:16]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 5906594-Cyano-2-fluorobenzoic acidHCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Produkt 1

HCID 10181017n-{4-Chloro-2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}(2-fluoro-4-cyanophenyl)carboxamideAusbeute 111,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-4-cyanobenzoic acid (1 g, 6.06 mmol) in thionyl chloride (5 ml) was refluxed for 2 hr. After concentration, the residue was dissolved in dichloromethane (5 ml). And a solution of the compound of (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (1.2 g, 4.25 mmol) in dichloromethane (10 ml) and pyridine (1.47 ml, 18.18 mmol) were added. The mixture was stirred at r.t. overnight. The precipitate was filtered and washed with a little amount of dichloromethane to give N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(2-fluoro-4-cyanophenyl)carboxamide (2.03 g, 78%). MS found for C20H11Cl2FN4O2 M+=429, (M+2)+=431.

Aufarbeitung

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. filtrationThe precipitate was filtered
  4. washwashed with a little amount of dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-48fd1d68fa0249118488f86d53172bd6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727981B2

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