2-Chloro-4-methanesulfonamidobenzoic acid → 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonamido)benzamide

HRID 923044Notes

Reaction equation

HRID 923044 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][C:19]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.ClC1C=C(NS(C)(=O)=O)C=CC=1C(O)=O>>[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([Cl:17])=[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:20]=1)=[O:6]

Participants

4

Reactant 3

HCID 183504972-Chloro-4-methanesulfonamidobenzoic acidHCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 54238017Methyl 2-chloro-4-(methylsulfonamido)benzoate

Product 1

HCID 529483472-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonamido)benzamide

Procedure

4.2 g of methyl 2-chloro-4-(methylsulfonamido)benzoate was hydrolyzed via Procedure M. 1 g of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 1.35 g of 2-chloro-4-(methylsulfonamido)benzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonamido)benzamide. MS (Q1) 436.1 (M)+.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4ee8fd0de1624ebf98cf721fabbbc037
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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