p-Toluenesulfonic acid monohydrate → N1-[4-(3,5-bis-trifluoromethyl-benzyl)-2-methylphenyl]-3-iodo-N2-((S)-1-methyl-2-methylthioethyl) phthalamide

HRID 1640095Notes

Reaction equation

HRID 1640095 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[C:11]([NH:13][C@@H:14]([CH3:18])[CH2:15][S:16][CH3:17])=[O:12].Cl.CN(C)CCCN1C=CN(C(N2C=CN(CC)C2)=O)C1.[F:40][C:41]([F:62])([F:61])[C:42]1[CH:43]=[C:44]([CH:54]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:56]=1)[CH2:45][C:46]1[CH:52]=[CH:51][C:49]([NH2:50])=[C:48]([CH3:53])[CH:47]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[F:40][C:41]([F:61])([F:62])[C:42]1[CH:43]=[C:44]([CH:54]=[C:55]([C:57]([F:60])([F:59])[F:58])[CH:56]=1)[CH2:45][C:46]1[CH:52]=[CH:51][C:49]([NH:50][C:5](=[O:7])[C:4]2[C:3](=[C:2]([I:1])[CH:10]=[CH:9][CH:8]=2)[C:11]([NH:13][C@@H:14]([CH3:18])[CH2:15][S:16][CH3:17])=[O:12])=[C:48]([CH3:53])[CH:47]=1

Participants

6

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 120027444-(3,5-Bis-trifluoromethyl-benzyl)-2-methylanilineHCID 59672031(S)-3-iodo-N-(1-methyl-2-methylthioethyl)phthalamic acidHCID 131729436N-(3-dimethylaminopropyl)-N'-ethylcarbonyldimidazole hydrochloride

Product 1

HCID 12002650N1-[4-(3,5-bis-trifluoromethyl-benzyl)-2-methylphenyl]-3-iodo-N2-((S)-1-methyl-2-methylthioethyl) phthalamideYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Iodo-N-((S)-1-methyl-2-methylthioethyl)-phthalamic acid (0.38 g) and N-(3-dimethylaminopropyl)-N′-ethylcarbonyldimidazole hydrochloride (0.2 g) were stirred in methylene chloride (10 ml) at room temperature for 30 minutes. 4-(3,5-Bis-trifluoromethyl-benzyl)-2-methylaniline (0.3 g) and p-toluenesulfonic acid hydrate (0.02 g) were added thereto and stirred at room temperature for 3 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-[4-(3,5-bis-trifluoromethyl-benzyl)-2-methylphenyl]-3-iodo-N2-((S)-1-methyl-2-methylthioethyl) phthalamide (0.15 g).

Workup

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

Sources & evidence

ORD record
ord-b9432b8fdccc46ba8bf824c36bac7da1
Source dataset
uspto-grants-2012_02
Patent number
US08110689B2

Reaction notes

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