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

HRID 633158Notes

Reaction equation

HRID 633158 reaction equation
CN1C=NN=C1S(CC1C=CC(C(O)=O)=CC=1)=O.[CH3:19][N:20]1[CH:24]=[N:23][N:22]=[C:21]1[S:25]([CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][CH:30]=1)(=[O:27])=[O:26].[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:33](=[O:35])[C:32]2[CH:31]=[CH:30][C:29]([CH2:28][S:25]([C:21]3[N:20]([CH3:19])[CH:24]=[N:23][N:22]=3)(=[O:26])=[O:27])=[CH:37][CH:36]=2)=[CH:41][C:40]=1[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1

Participants

4

Reactant 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

Product 1

HCID 58614821N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzamide

Procedure

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 separated on reverse phase HPLC to give N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-((4-methyl-4H-1,2,4-triazol-3-ylsulfonyl)methyl)benzamide.

Workup

  1. customThe mixture was separated on reverse phase HPLC

Sources & evidence

ORD record
ord-9920d8a386484068a8f8715f6c0de510
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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