Methyl acetoacetate → (Rac)-5-(2-chloro-5-trifluoromethyl-phenyl)-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-2-methyl-1h-pyrrole-3-carboxylic acid cyclohexylamide

HRID 229875

Reaktionsgleichung

Reaktionsgleichung von HRID 229875
CO[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].Br[CH2:10][C:11]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[Cl:23])=O.[CH3:24][C:25]1([CH3:32])[O:29][CH:28]([CH2:30][NH2:31])[CH2:27][O:26]1.[CH:33]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:33]1([NH:39][C:3]([C:4]2[CH:10]=[C:11]([C:13]3[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=3[Cl:23])[N:31]([CH2:30][CH:28]3[CH2:27][O:26][C:25]([CH3:32])([CH3:24])[O:29]3)[C:5]=2[CH3:6])=[O:8])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Komponenten

5

Edukt 4

HCID 7757Methyl acetoacetateHCID 7965CyclohexylamineHCID 27831832-Chloro-5-(trifluoromethyl)phenacyl bromideHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-

Produkt 1

HCID 11698963(Rac)-5-(2-chloro-5-trifluoromethyl-phenyl)-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-2-methyl-1h-pyrrole-3-carboxylic acid cyclohexylamide

Versuchsvorschrift

The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-chloro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, 2,2-dimethyl-1,3-dioxolan-4-methylamine as R3—(CH2)m—NH2 and 1-cyclohexylamine as R1R2NH, MS (ISP) 499.4 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-636f9d7eb59c48f9b8bc1089236cbbe3
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563910B2

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