4-Chloro-3-(pyridin-2-yl)aniline → N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzamide

HRID 1364783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364783
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[S:7]([CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:8].CN1C=NN=C1S(CC1C=CC(C(O)=O)=CC=1)(=O)=O.[Cl:38][C:39]1[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][C:40]=1[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1>>[Cl:38][C:39]1[CH:45]=[CH:44][C:42]([NH:43][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([CH2:9][S:7]([C:3]3[N:2]([CH3:1])[CH:6]=[N:5][N:4]=3)=[O:8])=[CH:18][CH:17]=2)=[CH:41][C:40]=1[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1

Komponenten

4

Edukt 3

HCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 668955914-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acidHCID 668961684-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoic acid

Produkt 1

HCID 58614626N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzamide

Versuchsvorschrift

500 mg of methyl 4-(bromomethyl)benzoate was reacted with 4-methyl-4H-1,2,4-triazole-3-thiol via Procedure Q. 804 mg of methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylthio)methyl)benzoate was subsequently reacted via Procedure R to give an approximate 1:9 mixture of methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoate and methyl 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoate. The mixture of 740 mg was hydrolyzed via Procedure M to give 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acid and 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoic acid. 114 mg of the mixture of 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzoic acid and 4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzoic acid was coupled to 75 mg of 4-chloro-3-(pyridin-2-yl)aniline via Procedure G. The mixture was seperated on reverse phase HPLC to give N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((4-methyl-4H-1,2,4-triazol-3-ylsulfinyl)methyl)benzamide. MS (Q1) 452.3 (M)+.

Aufarbeitung

  1. customThe mixture was seperated on reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-50873ee9834647b282b2ced450b69db9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888364B2

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