4-Chloro-3-(pyridin-2-yl)aniline → HCID 58614886, compound

HRID 1364776Notes

Reaction equation

HRID 1364776 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.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([CH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)(=[O:23])=[O:22]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:29](=[O:30])[C:28]2[CH:27]=[CH:26][C:25]([CH2:24][S:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=3)(=[O:23])=[O:22])=[CH:33][CH:32]=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 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 66877913HCID 66877913, compound

Product 1

HCID 58614886HCID 58614886, compound

Procedure

260 mg of methyl 4-((pyridin-2-ylthio)methyl)benzoate was reacted via Procedure R to give methyl 4-((pyridin-2-ylsulfonyl)methyl)benzoate. 275 mg of methyl 4-((pyridin-2-ylsulfonyl)methyl)benzoate was hydrolyzed via Procedure M to give 4-((pyridin-2-ylsulfonyl)methyl)benzoic acid. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-((pyridin-2-ylsulfonyl)methyl)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-((pyridin-2-ylsulfonyl)methyl)benzamide. MS (Q1) 464.1 (M)+.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ecc21be54bb348f68a88dfab4dad5f2c
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

Loading…