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

HRID 229864

Reaktionsgleichung

Reaktionsgleichung von HRID 229864
CO[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]([F:23])([F:22])[F:21])=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]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]([F:23])([F:22])[F:21])[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 27786842-(Trifluoromethoxy)phenacyl bromideHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-

Produkt 1

HCID 11540250(Rac)-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-2-methyl-5-(2-trifluoromethoxy-phenyl)-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-(trifluoromethoxy)phenyl]-ethanone as compound of formula S, 2,2-dimethyl-1,3-dioxolan-4-methylamine as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 481.5 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-fa5f8df3af1341e4ab7f7cba652210d7
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563910B2

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