Methyl acetoacetate → (rac) 1-[1,4]Dioxan-2-ylmethyl-2-methyl-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 229865Notes

Reaction equation

HRID 229865 reaction equation
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.[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]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]([F:23])([F:22])[F:21])[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 27786842-(Trifluoromethoxy)phenacyl bromideHCID 37480641,4-Dioxan-2-ylmethanamine

Product 1

HCID 11712429(rac) 1-[1,4]Dioxan-2-ylmethyl-2-methyl-5-(2-trifluoromethoxy-phenyl)-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-(trifluoromethoxy)phenyl]-ethanone as compound of formula S, 1,4-dioxane-2-methanamine as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 467.5 (M+H)+.

Sources & evidence

ORD record
ord-f6a5ba4234b84af9be7dc724f55f2577
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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