5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide → 4-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 46259Notes

Reaction equation

HRID 46259 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH:5]=[CH:4][N:3]=1.[Cl:16][C:17]1[C:18](F)=[CH:19][C:20]([F:43])=[C:21]([S:23]([N:26](CC2C=CC(OC)=CC=2OC)[C:27]2[S:28][CH:29]=[N:30][N:31]=2)(=[O:25])=[O:24])[CH:22]=1>>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[O:15][C:18]2[C:17]([Cl:16])=[CH:22][C:21]([S:23]([NH:26][C:27]3[S:28][CH:29]=[N:30][N:31]=3)(=[O:24])=[O:25])=[C:20]([F:43])[CH:19]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 1360636192-(2-Aminopyridin-4-yl)-4-chlorophenol

Product 1

HCID 468415024-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

Procedure

The title compound was prepared from 2-(2-aminopyridin-4-yl)-4-chlorophenol, (Preparation 721) and 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 247) using a method analogous to that used in Preparation 669. Purification by semi-preparative HPLC using 15-100% MeOH/H2O yielded the title compound.

Workup

  1. customthat used in Preparation 669
  2. customPurification by semi-preparative HPLC

Sources & evidence

ORD record
ord-60317847c5b241b89b99391dbecc7e53
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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