Methyl acetoacetate → Cyclohexylmethyl-5-(2,5-difluoro-phenyl)-2-methyl-1H-pyrrole-3-carboxylic acid ((1RS,2RS)-2-hydroxy-cyclohexylmethyl)-amide

HRID 1593171

Reaktionsgleichung

Reaktionsgleichung von HRID 1593171
CO[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].Br[CH2:10][C:11]([C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[F:20])=O.[NH2:21][CH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]1[OH:29]>>[OH:29][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[CH2:22][NH:21][C:3]([C:4]1[CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[N:21]([CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:5]=1[CH3:6])=[O:8]

Komponenten

4

Edukt 3

HCID 7757Methyl acetoacetateHCID 27782642-Bromo-1-(2,5-difluorophenyl)ethanoneHCID 12483365cis-2-Aminomethyl-1-cyclohexanol

Produkt 1

HCID 72485423Cyclohexylmethyl-5-(2,5-difluoro-phenyl)-2-methyl-1H-pyrrole-3-carboxylic acid ((1RS,2RS)-2-hydroxy-cyclohexylmethyl)-amide

Versuchsvorschrift

The title compound was synthesized in analogy to Example 68, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-(2,5-difluorophenyl)-ethanone as compound of formula S, c-cyclohexyl-methylamine as R3—(CH2)m—NH2 and cis-2-aminomethyl-1-cyclohexanol as R1R2NH, MS (ISP) 445.4 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-5959582c121649259d6e19f11483009b
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294644B2

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