Methyl acetoacetate → 5-(2-Chloro-5-trifluoromethyl-phenyl)-1-(rac)-[1,4]dioxan-2-ylmethyl-2-methyl-1h-pyrrole-3-carboxylic acid ((1r,2r)-2-hydroxy-cyclohexyl)-amide

HRID 229876

Reaktionsgleichung

Reaktionsgleichung von HRID 229876
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.[O:24]1[CH2:29][CH2:28][O:27][CH2:26][CH:25]1[CH2:30][NH2:31].[NH2:32][C@@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]1[OH:39]>>[OH:39][C@@H:34]1[CH2:35][CH2:36][CH2:37][CH2:38][C@H:33]1[NH:32][C:3]([C:4]1[CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=2[Cl:23])[N:31]([CH2:30][CH:25]2[CH2:26][O:27][CH2:28][CH2:29][O:24]2)[C:5]=1[CH3:6])=[O:8]

Komponenten

5

Edukt 4

HCID 7757Methyl acetoacetateHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27831832-Chloro-5-(trifluoromethyl)phenacyl bromideHCID 37480641,4-Dioxan-2-ylmethanamine

Produkt 1

HCID 115769555-(2-Chloro-5-trifluoromethyl-phenyl)-1-(rac)-[1,4]dioxan-2-ylmethyl-2-methyl-1h-pyrrole-3-carboxylic acid ((1r,2r)-2-hydroxy-cyclohexyl)-amide

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, 1,4-dioxane-2-methanamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH, MS (ISP) 501.4 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-7677928d7be9466eab4c3a36cba5cc17
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563910B2

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