4-[(2-Amino-2-oxoethyl)sulfonyl]benzoic acid → HCID 58614735, compound

HRID 923067Notes

Reaction equation

HRID 923067 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.[NH2:15][C:16](=[O:30])[CH2:17][S:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>>[NH2:15][C:16](=[O:30])[CH2:17][S:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[CH:4]=2)=[O:26])=[CH:23][CH:22]=1)(=[O:19])=[O:20]

Participants

3

Reactant 2

HCID 246906774-[(2-Amino-2-oxoethyl)sulfonyl]benzoic acidHCID 401519254-Chloro-3-(pyridin-2-yl)aniline

Product 1

HCID 58614735HCID 58614735, compound

Procedure

2.5 g of 2-bromoacetamide was reacted with methyl 4-mercaptobenzoate via Procedure Q to afford methyl 4-(2-amino-2-oxoethylthio)benzoate. 2.6 g of methyl 4-(2-amino-2-oxoethylthio)benzoate was reacted via Procedure R to give methyl 4-(2-amino-2-oxoethylsulfonyl)benzoate. 1 g of methyl 4-(2-amino-2-oxoethylsulfonyl)benzoate was hydrolyzed via Procedure M to give 4-(2-amino-2-oxoethylsulfonyl)benzoic acid. 150 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-(2-amino-2-oxoethylsulfonyl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield 4-(2-amino-2-oxoethylsulfonyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. MS (Q1) 430.2 (M)+.

Workup

  1. customThe product was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-0d629fd85cf24750b6cfbc87ee1d3728
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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