Methyl 4,5-dimethoxyanthranilate → N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(4,5-dimethoxy-2-methoxycarbonylphenyl)aminocarbonyl]thiophene-3-sulfonamide

HRID 234469

Reaktionsgleichung

Reaktionsgleichung von HRID 234469
[Cl:1][C:2]1[C:3]([CH3:31])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16](NC1C=C2OCOC2=CC=1C(=O)C)=[O:17])(=[O:10])=[O:9].[CH3:32][O:33][C:34](=[O:46])[C:35]1[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[CH:37][C:36]=1[NH2:45]>>[Cl:1][C:2]1[C:3]([CH3:31])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]([NH:45][C:36]1[CH:37]=[C:38]([O:43][CH3:44])[C:39]([O:41][CH3:42])=[CH:40][C:35]=1[C:34]([O:33][CH3:32])=[O:46])=[O:17])(=[O:9])=[O:10].[S:13]1[CH:14]=[CH:15][C:11]([S:8]([NH2:7])(=[O:10])=[O:9])=[CH:12]1

Komponenten

4

Edukt 2

HCID 611144Methyl 4,5-dimethoxyanthranilateHCID 10696210N-(4-chloro-3-methyl-5-isoxazolyl)2-{[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide

Produkt 2

HCID 1201388Thiophene-3-sulfonamideAusbeute 1 %HCID 10839579N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(4,5-dimethoxy-2-methoxycarbonylphenyl)aminocarbonyl]thiophene-3-sulfonamideAusbeute 13 %

Versuchsvorschrift

The title compounds were prepared by the method set forth for N-(4-chloro-3-methyl-5-isoxazolyl)2-{[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide (EXAMPLE 148) except that methyl-2-amino-4,5-dimethoxybenzoate was used instead of 2'-amino-4',5'-(methylenedioxy)acetophenone. The crude product was purified via HPLC to give N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(4,5-dimethoxy-2-methoxycarbonylphenyl)aminocarbonyl]thiophene-3-sulfonamide as a yellow powder (13% yield, m.p. 167°-168° C.) and N-(4-chloro-3-methyl-5-isoxazolyl)2-{[4,5-dimethoxy-2,4,5-dimethoxy-2-methoxycarbonyl)phenyl]phenylaminocarbonyl}thiophene-3-sulfonamide as a dull yellow solid (1% yield, m.p. 228°-230° C.).

Aufarbeitung

  1. customThe crude product was purified via HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cd9d1d478693487d92c1dd7ef1c2477f
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594021

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