Methanesulfonamide → N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(methylsulfonamido)nicotinamide

HRID 1364798Notes

Reaction equation

HRID 1364798 reaction equation
Cl[C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:10]=2)=[O:7])=[CH:4][N:3]=1.[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26]>C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:22]=[CH:23][C:2]([NH:28][S:25]([CH3:24])(=[O:27])=[O:26])=[N:3][CH:4]=2)=[CH:10][C:11]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 586148106-Chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]pyridine-3-carboxamide

Product 1

HCID 58614869N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(methylsulfonamido)nicotinamide

Reagents, catalysts & solvents 1

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineSolvent

Procedure

100 mg of 6-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)nicotinamide was reacted with methanesulfonamide and 108 μL of 2-tert-Butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine via Procedure F. The crude reaction was concentrated to dryness and purified by reverse phase HPLC to give pure N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(methylsulfonamido)nicotinamide. MS (Q1) 403 (M)+.

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated to dryness
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-666a9fdbb4ce4f3abc148d286523a5c0
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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