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

HRID 229874Notes

Reaction equation

HRID 229874 reaction equation
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].[CH:32]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([NH:38][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:25]3[CH2:26][O:27][CH2:28][CH2:29][O:24]3)[C:5]=2[CH3:6])=[O:8])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 4

HCID 7757Methyl acetoacetateHCID 7965CyclohexylamineHCID 27831832-Chloro-5-(trifluoromethyl)phenacyl bromideHCID 37480641,4-Dioxan-2-ylmethanamine

Product 1

HCID 11677461(Rac)-5-(2-chloro-5-trifluoromethyl-phenyl)-1-[1,4]dioxan-2-ylmethyl-2-methyl-1h-pyrrole-3-carboxylic acid cyclohexylamide

Procedure

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 cyclohexylamine as R1R2NH, MS (ISP) 485.5 (M+H)+.

Sources & evidence

ORD record
ord-1df8192974834111968a5eb183ff64a9
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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