Benzenesulfonamide, 3-amino- → 2-(2-Methylpyridin-3-yloxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide

HRID 79101

Reaktionsgleichung

Reaktionsgleichung von HRID 79101
OC(C(F)(F)F)=O.[CH3:8][C:9]1[C:14]([O:15][C:16]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:17]=2[C:18]([OH:20])=O)=[CH:13][CH:12]=[CH:11][N:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:53][C:54]1[CH:55]=[C:56]([S:60]([NH2:63])(=[O:62])=[O:61])[CH:57]=[CH:58][CH:59]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:8][C:9]1[C:14]([O:15][C:16]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:17]=2[C:18]([NH:53][C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([S:60](=[O:62])(=[O:61])[NH2:63])[CH:55]=2)=[O:20])=[CH:13][CH:12]=[CH:11][N:10]=1

Komponenten

6

Edukt 4

HCID 7377Benzenesulfonamide, 3-amino-HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1317318842-(2-methylpyridin-3-yloxy)-4-(trifluoromethyl)benzoic acid TFA salt

Produkt 1

HCID 248553752-(2-Methylpyridin-3-yloxy)-n-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-(2-methylpyridin-3-yloxy)-4-(trifluoromethyl)benzoic acid TFA salt (54 mg, 0.13 mmol) and HATU (50 mg, 0.13 mmol) in DMF (1 mL) was stirred at room temperature 3 min. To this solution was added 3-amino-benzenesulfonamide (23 mg, 0.13 mmol) and triethylamine (46 μL, 0.33 mmol). The reaction was stirred at room temperature for 16 h and purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 2-(2-methylpyridin-3-yloxy)-N-(3-sulfamoylphenyl)-4-(trifluoromethyl)benzamide. LC/MS: m/z 452.3 (M+H)+ at 1.07 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Aufarbeitung

  1. custompurified by preparative reverse phase

Quellen und Nachweise

ORD-Eintrag
ord-9921ceb924de4fe59aebfb9a00a89807
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841483B2

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