5-(5-chloro-1,2,4-thiadiazol-3-yl)thiophene-2-sulfonyl Chloride → 5-(5-chloro-1,2,4-thiadiazol-3-yl)-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)thiophene-2-sulfonamide

HRID 73400Notes

Reaction equation

HRID 73400 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])[C:5]([NH2:18])=[CH:4][CH:3]=1.[Cl:19][C:20]1[S:24][N:23]=[C:22]([C:25]2[S:29][C:28]([S:30](Cl)(=[O:32])=[O:31])=[CH:27][CH:26]=2)[N:21]=1>>[Cl:19][C:20]1[S:24][N:23]=[C:22]([C:25]2[S:29][C:28]([S:30]([NH:18][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[C:7]([F:8])[C:6]=3[NH:9][C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=3[F:17])(=[O:32])=[O:31])=[CH:27][CH:26]=2)[N:21]=1

Participants

3

Reactant 2

HCID 27358205-(5-chloro-1,2,4-thiadiazol-3-yl)thiophene-2-sulfonyl ChlorideHCID 593863065,6-difluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine

Product 1

HCID 534920155-(5-chloro-1,2,4-thiadiazol-3-yl)-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)thiophene-2-sulfonamide

Procedure

According to the general procedure B, 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine (0.182 mmol) was reacted with 5-(5-chloro-1,2,4-thiadiazol-3-yl)thiophene-2-sulfonyl chloride (0.5 mmol) to obtain 5-(5-chloro-1,2,4-thiadiazol-3-yl)-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)thiophene-2-sulfonamide. 1H NMR (300 MHz, CDCl3)) δ 5.8 (dt, 1H), 5.95 (s, 1H), 6.95 (d, 1H), 7.4 (m, 2H), 7.6 (d, 1H), 7.8 (s, 1H).

Sources & evidence

ORD record
ord-2509433da39342408fdd6a58d92ab23e
Source dataset
uspto-grants-2014_09
Patent number
US08829052B2

Reaction notes

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