3-(Trifluoromethyl)phenyl isocyanate → Methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)thiazole-2-carboxamido)butanoate

HRID 1024440

Reaktionsgleichung

Reaktionsgleichung von HRID 1024440
[CH3:1][CH:2]([CH3:25])[CH:3]([NH:8][C:9]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5].[N:26]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)=[C:27]=[O:28]>C1COCC1>[CH3:1][CH:2]([CH3:25])[CH:3]([NH:8][C:9]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:27]([NH:26][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:36])([F:37])[F:38])[CH:30]=3)=[O:28])=[CH:18][CH:17]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Produkt 1

HCID 52934364Methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)thiazole-2-carboxamido)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 120 mg) in THF (2.4 ml) was added 1-isocyanato-3-(trifluoromethyl)benzene (101 mg) and the mixture was stirred overnight at RT. The mixture was concentrated, purified by column chromatography (EtOAc:Pet ether, 2:8) and crystallized in CHCl3/pet ether to give the title compound. Yield: 156 mg (83%); 1HNMR (DMSO-d6, 300 MHz): δ 9.12 (s, 1H), 9.08 (s, 1H), 8.36 (s, 1H), 8.03 (d, 1H), 7.74 (d, 2H), 7.61 (d, 2H), 7.55 (dd, 1H), 7.5 (m, 1H), 7.32 (dd, 1H), 4.33 (m, 1H), 3.68 (s, 3H), 2.26 (m, 1H), 0.92 (d, 6H); MS (ES+): m/z 521 (M+1).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography (EtOAc:Pet ether, 2:8)
  3. customcrystallized in CHCl3/pet ether

Quellen und Nachweise

ORD-Eintrag
ord-3c3a7f1bd3c14a1390b344efdbca2d0c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722901B2

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