5-Methylthiophene-2-sulfonyl chloride → N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-5-methylthiophene-2-sulfonamide

HRID 73409Notes

Reaction equation

HRID 73409 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.[CH3:19][C:20]1[S:24][C:23]([S:25](Cl)(=[O:27])=[O:26])=[CH:22][CH:21]=1>>[F:8][C:7]1[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])=[C:5]([NH:18][S:25]([C:23]2[S:24][C:20]([CH3:19])=[CH:21][CH:22]=2)(=[O:27])=[O:26])[CH:4]=[CH:3][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 124001125-Methylthiophene-2-sulfonyl chlorideHCID 593863065,6-difluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine

Product 1

HCID 53492224N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-5-methylthiophene-2-sulfonamide

Procedure

According to the general procedure B, 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine was reacted with 5-methylthiophene-2-sulfonyl chloride to obtain the title compound. 1H NMR (300 MHz, CDCl3); δ 7.34 (dd, J=0.9 & 10.2 Hz, 1H), 7.30 (ddd, J=2.1, 4.8 & 9.0 Hz, 1H), 7.25 (d, J=3.9 Hz, 1H), 7.07 (m, 2H), 6.65 (dd, J=1.2 & 3.9 Hz, 1H), 5.89 (dt, J=2.4, 8.7 & 17.4 Hz, 1H), 5.54 (br s, D2O exchangeable, 1H), 2.46 (s, 3H).

Sources & evidence

ORD record
ord-9757d764abca4e619cad0569867855f0
Source dataset
uspto-grants-2014_09
Patent number
US08829052B2

Reaction notes

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