3-(1,1-Dimethyl-2-methylsulfanyl-ethylimino)-4-iodo-3H-isobenzofuran-1-one → N1-[4-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-methylphenyl]-N2-(1,1-dimethyl-2-methylsulfanylethyl)-3-iodophthalamide

HRID 2243242Notes

Reaction equation

[CH3:1][C:2]([N:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[I:17])[C:10](=[O:18])[O:9]1)([CH3:6])[CH2:3][S:4][CH3:5].[CH3:19][C:20]1[CH:21]=[C:22]([CH:37]=[CH:38][C:39]=1[NH2:40])[CH2:23][N:24]1[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][C:26]([C:33]([F:36])([F:35])[F:34])=[N:25]1>C(#N)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:36][C:33]([F:34])([F:35])[C:26]1[CH:27]=[C:28]([C:29]([F:32])([F:30])[F:31])[N:24]([CH2:23][C:22]2[CH:37]=[CH:38][C:39]([NH:40][C:10](=[O:18])[C:11]3[C:16](=[C:15]([I:17])[CH:14]=[CH:13][CH:12]=3)[C:8]([NH:7][C:2]([CH3:6])([CH3:1])[CH2:3][S:4][CH3:5])=[O:9])=[C:20]([CH3:19])[CH:21]=2)[N:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(1,1-Dimethyl-2-methylsulfanyl-ethylimino)-4-iodo-3H-isobenzofuran-1-one (0.53 g) and 1-(3-methyl-4-aminobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (0.45 g) were dissolved in acetonitrile (15 ml), to which p-toluenesulfonic acid monohydrate (0.01 g) was added and the mixture was stirred at 60° C. for 3 hours. After finishing the reaction, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain N1-[4-(3,5-bistrifluoromethylpyrazol-1-ylmethyl)-2-methylphenyl]-N2-(1,1-dimethyl-2-methylsulfanylethyl)-3-iodophthalamide (0.91 g). mp. 83-87° C.

Workup

additionwas added
customthe reaction
distillationthe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-bb6e2c81ffef4710ba047869401035b7
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674807B2

Reaction notes

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