Sulfuryl chloride → 1-Allyl-cyclopropanesulfonic acid [3,4,6-trifluoro-2-(2-fluoro-4-iodo-phenylamino)phenyl]-amide

HRID 508143

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])[C:3]=1[NH2:19].S(Cl)(Cl)(=O)=O.[CH2:25]([C:28]1([S:31](Cl)(=[O:33])=[O:32])[CH2:30][CH2:29]1)[CH:26]=[CH2:27]>N1C=CC=CC=1>[F:9][C:5]1[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])=[C:3]([NH:19][S:31]([C:28]2([CH2:25][CH:26]=[CH2:27])[CH2:30][CH2:29]2)(=[O:33])=[O:32])[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of the amine, i.e., 3,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine, (1 eq) in anhydrous pyridine (5 ml/mmole) was added the sulfonyl chloride, i.e., 1-allyl-cyclopropanesulfonyl chloride, (1-5 eq). The reaction mixture was stirred at 40° C. for 48 hours. The reaction mixture was partitioned with water and EtOAc. The organic layer was washed with brine, dried (MGSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica. 1H NMR (CDCl3, 300 MHz): δ 7.41 (dd, 1H), 7.38 (dd, 1H), 7.09 (s, 1H), 6.78 (m, 1H), 6.49 (m, 1H), 5.96 (s, 1H), 5.86 (m, 1H), 5.18 (d, 2H), 2.76 (d, 2H), 1.23 (m, 2H), 0.872 (m, 2H).

Workup

customThe reaction mixture was partitioned with water and EtOAc
washThe organic layer was washed with brine
customdried (MGSO4)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record: ord-182caf2807d84ef799efe0560e10dc7d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09095581B2

Linked notes

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