2-Amino-4,5-dimethoxybenzonitrile → N-(4-chloro-3-methyl-5-isoxazolyl)-2-[{2-cyano-4, 5-dimethoxyphenyl)aminocarbonyl]-thiophene-3-sulfonamide

HRID 234471

Reaction equation

HRID 234471 reaction equation
[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].[NH2:32][C:33]1[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[CH:37][C:34]=1[C:35]#[N:36]>>[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:32][C:33]1[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[CH:37][C:34]=1[C:35]#[N:36])=[O:17])(=[O:9])=[O:10]

Participants

3

Reactant 2

HCID 7359672-Amino-4,5-dimethoxybenzonitrileHCID 10696210N-(4-chloro-3-methyl-5-isoxazolyl)2-{[2-acetyl-4,5-(methylenedioxy)phenyl]aminocarbonyl}thiophene-3-sulfonamide

Product 1

HCID 9956918N-(4-chloro-3-methyl-5-isoxazolyl)-2-[{2-cyano-4, 5-dimethoxyphenyl)aminocarbonyl]-thiophene-3-sulfonamide

Procedure

N-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-cyano-4,5-dimethoxyphenyl)aminocarbonyl]thiophene-3-sulfonamide was 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 2-amino-4,5-dimethoxybenzonitrile was used instead of 2'-amino-4',5'-(methylenedioxy)acetophenone. N-(4-chloro-3-methyl-5-isoxazolyl)-2-[{2-cyano-4,5-dimethoxyphenyl)aminocarbonyl]thiophene-3-sulfonamide was obtained via HPLC purification as a light brown powder (36% yield, m.p. 53°-56° C.).

Workup

  1. customN-(4-chloro-3-methyl-5-isoxazolyl)-2-[(2-cyano-4,5-dimethoxyphenyl)aminocarbonyl]thiophene-3-sulfonamide was prepared by the method

Sources & evidence

ORD record
ord-05c784d4bf2d499ca2faa00f6bef4363
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Linked notes

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