Benzenesulfonamide, 3-amino- → 2-cyclohexyl-N-(3-(aminosulfonyl)phenyl)benzamide

HRID 79095

Reaktionsgleichung

Reaktionsgleichung von HRID 79095
[CH:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:40][C:41]1[CH:42]=[C:43]([S:47]([NH2:50])(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=1.C(N(CC)CC)C>CN(C=O)C>[CH:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([S:47]([NH2:50])(=[O:48])=[O:49])[CH:42]=2)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 4

HCID 7377Benzenesulfonamide, 3-amino-HCID 8471TriethylamineHCID 70205722-cyclohexylbenzoic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 248552642-cyclohexyl-N-(3-(aminosulfonyl)phenyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-cyclohexyl benzoic acid (20 mg, 0.10 mmol) and HATU (38 mg, 0.10 mmol) in DMF (1 mL) was stirred at room temperature 3 min. To this solution was added 3-amino-benzenesulfonamide (17 mg, 0.10 mmol) and triethylamine (14 μL, 0.10 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-cyclohexyl-N-(3-(aminosulfonyl)phenyl)benzamide. LC/MS: m/z 359.1 (M+H)+ at 3.85 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Aufarbeitung

  1. custompurified by preparative reverse phase

Quellen und Nachweise

ORD-Eintrag
ord-7c0b71d177244859a5b82e65e13df75e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841483B2

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