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

HRID 229858Notes

Reaction equation

HRID 229858 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]([Cl:19])[C:16]([CH3:20])=[CH:15][C:14]=1[O:21][CH3:22])=O.[O:23]1[CH2:28][CH2:27][O:26][CH2:25][CH:24]1[CH2:29][NH2:30].[N:31]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[N:31]1([NH:37][C:3]([C:4]2[CH:10]=[C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[C:16]([CH3:20])=[CH:15][C:14]=3[O:21][CH3:22])[N:30]([CH2:29][CH:24]3[CH2:25][O:26][CH2:27][CH2:28][O:23]3)[C:5]=2[CH3:6])=[O:8])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 4

HCID 7757Methyl acetoacetateHCID 166581-AminopiperidineHCID 27568882-Bromo-1-(5-chloro-2-methoxy-4-methylphenyl)ethanoneHCID 37480641,4-Dioxan-2-ylmethanamine

Product 1

HCID 11590743Rac-5-(5-chloro-2-methoxy-4-methyl-phenyl)-1-[1,4]dioxan-2-ylmethyl-2-methyl-1h-pyrrole-3-carboxylic acid piperidin-1-ylamide

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-(5-chloro-2-methoxy-4-methyl-phenyl)-ethanone (purchased from Oakwood) as compound of formula S, rac-1,4-dioxane-2-methanamine as R3—(CH2)m—NH2 and piperidine-1-ylamine as R1R2NH, MS (ISP) 462.2 (M+H)+.

Sources & evidence

ORD record
ord-35626689a35c4dd09bc9fb92596f41a5
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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