Dichloromethane → 5-Chloro-2-fluoro-4-[5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 46271Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([O:36][C:37]2[CH:42]=[C:41]([F:43])[C:40]([C:44]([F:47])([F:46])[F:45])=[CH:39][C:38]=2[C:48]2[CH:53]=[CH:52][N:51]=[N:50][CH:49]=2)=[CH:11][C:12]([F:35])=[C:13]([S:15]([N:18](CC2C=CC(OC)=CC=2OC)[C:19]2[S:20][CH:21]=[N:22][N:23]=2)(=[O:17])=[O:16])[CH:14]=1.C(Cl)Cl>>[Cl:8][C:9]1[C:10]([O:36][C:37]2[CH:42]=[C:41]([F:43])[C:40]([C:44]([F:45])([F:46])[F:47])=[CH:39][C:38]=2[C:48]2[CH:53]=[CH:52][N:51]=[N:50][CH:49]=2)=[CH:11][C:12]([F:35])=[C:13]([S:15]([NH:18][C:19]2[S:20][CH:21]=[N:22][N:23]=2)(=[O:16])=[O:17])[CH:14]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 866438255-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-[5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

Product 1

HCID 468419375-Chloro-2-fluoro-4-[5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamideYield 34.7%

Procedure

Trifluoroacetic acid (500 uL, 6 mmol) was added to a solution of 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-[5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (22 mg) in methylene chloride (5 mL, 70 mmol). After stirring 20 min, the reaction mixture was concentrated onto diatomaceous earth and purified by automated flash chromatography (4 g SiO2, methylene chloride to 9:1 methylene chloride-methanol) to afford the product as a tan solid (6 mg, 9%).

Workup

concentrationthe reaction mixture was concentrated onto diatomaceous earth
custompurified by automated flash chromatography (4 g SiO2, methylene chloride to 9:1 methylene chloride-methanol)

Sources & evidence

ORD record: ord-715fe3ae9b634217a9caeed16ab30128
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541588B2

Reaction notes

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