Methanesulfonamide → 5-Chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamide

HRID 2048017Notes

Reaction equation

HRID 2048017 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[N:15][C:16]([F:20])=[C:17]([Cl:19])[CH:18]=2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.CN(C)CCCN=C=NCC.[CH3:33][S:34]([NH2:37])(=[O:36])=[O:35]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[N:15][C:16]([F:20])=[C:17]([Cl:19])[CH:18]=2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:37][S:34]([CH3:33])(=[O:36])=[O:35])=[O:8]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666665425-Chloro-4-(5-chloro-6-fluoropyridin-3-yloxy)-2-fluorobenzoic acid

Product 1

HCID 580424375-Chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamideYield 57.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Chloro-4-(5-chloro-6-fluoropyridin-3-yloxy)-2-fluorobenzoic acid (Preparation 162, 6.100 g, 19.60 mmol), 4-dimethylaminopyridine (2.330 g, 19.06 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (5.480 g, 28.59 mmol) and methanesulfonamide (2.720 g, 28.59 mmol) were suspended in DCM (20 mL). The reaction mixture was stirred at room temperature for 18 hours, quenched with aqueous 1M HCl and extracted with EtOAc. Combined organics were concentrated in vacuo. The resulting residue was purified by reverse phase chromatography to afford the title compound as a white solid (4.50 g):

Workup

  1. customquenched with aqueous 1M HCl
  2. extractionextracted with EtOAc
  3. concentrationCombined organics were concentrated in vacuo
  4. customThe resulting residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-1f3db8d1bf79426893e3a64046067487
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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