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

HRID 1640095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640095
[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

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b9432b8fdccc46ba8bf824c36bac7da1
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110689B2

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