Sulfanilamide → 2-[4,5-Dibromo-3-(3-cyano-5-difluoromethyl-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

HRID 2192746Notes

Reaction equation

HRID 2192746 reaction equation
C(O[C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[C:9]([Br:13])=[C:8]([O:14][C:15]2[CH:20]=[C:19]([CH:21]([F:23])[F:22])[CH:18]=[C:17]([C:24]#[N:25])[CH:16]=2)[C:7]=1[F:26])C.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:31][C:30]=1[CH3:39].NC1C=CC(S(N)(=O)=O)=CC=1>>[Br:13][C:9]1[C:10]([Br:12])=[CH:11][C:6]([CH2:5][C:4]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([S:35](=[O:37])(=[O:36])[NH2:38])=[CH:31][C:30]=2[CH3:39])=[O:27])=[C:7]([F:26])[C:8]=1[O:14][C:15]1[CH:20]=[C:19]([CH:21]([F:22])[F:23])[CH:18]=[C:17]([C:24]#[N:25])[CH:16]=1

Participants

4

Reactant 3

HCID 5333SulfanilamideHCID 1430374-Amino-3-methylbenzene-1-sulfonamideHCID 86601306[4,5-Dibromo-3-(3-cyano-5-difluoromethyl-phenoxy)-2-fluoro-phenyl]-acetic acid ethyl ester

Product 1

HCID 210796672-[4,5-Dibromo-3-(3-cyano-5-difluoromethyl-phenoxy)-2-fluoro-phenyl]-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide

Procedure

[4,5-Dibromo-3-(3-cyano-5-difluoromethyl-phenoxy)-2-fluoro-phenyl]-acetic acid ethyl ester (200) was isolated as a byproduct in the Sandmeyer reaction used in the preparation of 186 described in step 1 of example 40. The dibromo compound was converted to I-104 by the procedure described in steps 7 to 9 of example 1 except in the present example, 4-amino-3-methyl-benzenesulfonamide replaced 4-amino-benzenesulfonamide.

Sources & evidence

ORD record
ord-3c51f0fe21dc4a118f9db96098c6c542
Source dataset
uspto-grants-2012_12
Patent number
US08329755B2

Reaction notes

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