4-[methyl(methylsulfonyl)amino]benzoic acid → HCID 58614856, compound

HRID 1364778Notes

Reaction equation

HRID 1364778 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[CH3:15][N:16]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)[S:17]([CH3:20])(=[O:19])=[O:18]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([N:16]([CH3:15])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:22][CH:23]=2)=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 18093724-[methyl(methylsulfonyl)amino]benzoic acidHCID 401519254-Chloro-3-(pyridin-2-yl)aniline

Product 1

HCID 58614856HCID 58614856, compound

Procedure

500 mg of methyl 4-(methylamino)benzoate was cooled to 0° C. in DCM with 270 μL of Pyridine before 260 μL Methanesulfonyl Chloride was added dropwise. Reaction was allowed to warm to room temperature and stir overnight. Solvent was concentrated and the crude material was dissolved in Ethyl Acetate and extracted with 0.1N NaOH solution twice. Crude material was dried over Magnesium Sulfate, filtered and concentrated to give methyl 4-(N-methylmethylsulfonamido)benzoate. 698 mg of methyl 4-(N-methylmethylsulfonamido)benzoate was hydrolyzed via Procedure M to give 4-(N-methylmethylsulfonamido)benzoic acid. 100 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-(N-methylmethylsulfonamido)benzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield pure N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(N-methylmethylsulfonamido)benzamide. MS (Q1) 416.3 (M)+.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5d63a8a06a7e4f72b9960c5524542b5a
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

Loading…