HCID 57450847, compound → Phthalamide

HRID 1640096Notes

Reaction equation

HRID 1640096 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[N:12][C@@H](C)CSC)[O:5][C:6]2=[O:11].FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CC1[N:29]=C(C)C(N)=CC=1>C(#N)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:6]([NH2:29])(=[O:11])[C:7]1[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=1)[C:4]([NH2:12])=[O:5]

Participants

5

Reactant 2

HCID 57450847HCID 57450847, compoundHCID 86639782HCID 86639782, compound

Product 1

HCID 6956PhthalamideYield 194.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-3-[(S)-1-methyl-2-methylthioethylimino]-3-H-isobenzofuran-1-one (0.2 g) and 6-(3,5-bis-trifluoromethyl-benzyl)-2-methyl-pyridin-3-ylamine (0.22 g) were dissolved in acetonitrile (10 ml), to which p-toluenesulfonic acid hydrate (0.01 g) was added, and stirred at 60° C. for 20 hours. After the reaction, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain N1-[6-3,5-bis-trifluoromethyl-benzyl)-2-methyl-pyridin-3-yl]-3-chloro-N2-(S)-1-methyl-2-methylhioethyl)phthalamide (0.21 g).

Workup

  1. additionwas added
  2. customAfter the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-119172765e964c5d8ea2b4d10d6daf3c
Source dataset
uspto-grants-2012_02
Patent number
US08110689B2

Reaction notes

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