Cyclobutanesulfonyl chloride → N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)cyclobutanesulfonamide

HRID 424010Notes

Reaction equation

[CH:1]1([S:5](Cl)(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.[F:9][C:10]1[C:15]([F:16])=[C:14]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])[C:13]([NH2:26])=[C:12]([O:27][CH3:28])[CH:11]=1>>[F:16][C:15]1[C:14]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[C:13]([NH:26][S:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:7])=[O:6])[C:12]([O:27][CH3:28])=[CH:11][C:10]=1[F:9]

Participants

Reactant 2

HCID 22636930Cyclobutanesulfonyl chloride

HCID 532609665,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine

Product 1

HCID 53492296N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)cyclobutanesulfonamideYield 75%

Procedure

According to the general procedure B, the cyclobutylsulfonyl chloride prepared in the step above was reacted with 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxy-benzene-1,2-diamine to obtain the title product. Yield: 75%. 1H-NMR (300 MHz, CDCl3): δ=7.44 (s, 1H, br), 7.41-7.36 (dd, 1H), 7.24-7.23 (m, 1H), 6.54-6.38 (m, 2H), 5.90 (s, 1H, br), 3.85-3.75 (m, 5H), 2.60-2.40 (m, 2H), 2.25-2.15 (m, 1H), 2.15-1.95 (m, 2H); m/z=511 [M−1]−.

Sources & evidence

ORD record: ord-0d4fbae660d3402db250d87eb123ad8c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101799B2

Reaction notes

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