4-Amino-3-chlorobenzenesulfonamide → HCID 49768067, compound

HRID 132795Notes

Reaction equation

HRID 132795 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH3:13])[C:7]=1[CH3:14])[CH3:2].[CH3:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1F)[C:20]#[N:21].[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][C:28]=1[Cl:37]>C(OC(=O)C)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH3:13])[C:7]=1[CH3:14])[CH3:2].[Cl:37][C:28]1[CH:29]=[C:30]([S:33](=[O:34])(=[O:35])[NH2:36])[CH:31]=[CH:32][C:27]=1[NH:26][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:24]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=2[CH3:16])=[C:8]([CH3:13])[C:7]=1[CH3:14]

Participants

6

Reactant 3

HCID 15020144-Amino-3-chlorobenzenesulfonamideHCID 27791804-Fluoro-3-methylbenzonitrileHCID 58856157HCID 58856157, compound2×

Product 2

HCID 49768067HCID 49768067, compoundHCID 58856157HCID 58856157, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(4-Hydroxy-2,3-dimethyl-phenyl)-acetic acid ethyl ester (45c) was prepared as described in Example 13. N-(2-Chloro-4-sulfamoyl-phenyl)-2-[4-(4-cyano-2-methyl-phenoxy)-2,3-dimethyl-phenyl]-acetamide (I-25) was prepared starting with 45c utilizing the procedure from example 1 except in step 1, 45c was used in place of 3-bromo-4-hydroxy-phenyl)-acetic acid ethyl ester and 3-methyl-4-fluoro-benzonitrile was used in place of 3-chloro-5-fluoro-benzonitrile and in step 4, 4-amino-3-chloro-benzenesulfonamide was used in place of 4-amino-benzenesulfonamide.

Sources & evidence

ORD record
ord-714b8a1666ce40c4a7f8f75fcb75cdb8
Source dataset
uspto-grants-2008_06
Patent number
US07388111B2

Reaction notes

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