(NE)-5-chloro-N-[1-(ethoxymethyl)pyrimidin-4-ylidene]-2,4-difluorobenzenesulfonamide → 4-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

HRID 1401924Notes

Reaction equation

HRID 1401924 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:22])=[C:6]([S:8]([N:11](COCC)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.ClC1C(F)=CC(F)=C(S(/N=C2/N=CN(COCC)C=C/2)(=O)=O)C=1.[NH2:47][C:48]1[CH:53]=[C:52]([C:54]2[CH:59]=[C:58]([Cl:60])[CH:57]=[CH:56][C:55]=2[OH:61])[CH:51]=[CH:50][N:49]=1>>[NH2:47][C:48]1[CH:53]=[C:52]([C:54]2[CH:59]=[C:58]([Cl:60])[CH:57]=[CH:56][C:55]=2[O:61][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][N:13]=3)(=[O:9])=[O:10])=[C:5]([F:22])[CH:4]=2)[CH:51]=[CH:50][N:49]=1

Participants

4

Reactant 3

HCID 59436509(NE)-5-chloro-N-[1-(ethoxymethyl)pyrimidin-4-ylidene]-2,4-difluorobenzenesulfonamide2×HCID 594366195-chloro-N-(ethoxymethyl)-2,4-difluoro-N-pyrimidin-4-ylbenzenesulfonamideHCID 1360636192-(2-Aminopyridin-4-yl)-4-chlorophenol

Product 1

HCID 468415004-[2-(2-aminopyridin-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

Procedure

The title compound was prepared by analogy with the method used for Example 813 below using 5-chloro-N-(ethoxymethyl)-2,4-difluoro-N-pyrimidin-4-ylbenzenesulfonamide, 5-chloro-N-[(4E)-1-(ethoxymethyl)pyrimidin-4(1H)-ylidene]-2,4-difluorobenzenesulfonamide and 5-chloro-N-[(4E)-1-(ethoxymethyl)pyrimidin-4(1H)-ylidene]-2,4-difluorobenzenesulfonamide, (Preparation 719) used as a mixture of three regioisomers and 2-(2-aminopyridin-4-yl)-4-chlorophenol (Preparation 721).

Sources & evidence

ORD record
ord-417cf820c65f41fabfca1ff38e82efc1
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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