Methyl acetoacetate → 5-(5-Chloro-2-methoxy-4-methyl-phenyl)-1-(2-cyclopropyl-ethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 2105811Notes

Reaction equation

HRID 2105811 reaction equation
C[O:2][C:3](=O)[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.[CH:23]1([CH2:26][CH2:27][NH2:28])[CH2:25][CH2:24]1.[CH:29]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([NH:35][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:28]([CH2:27][CH2:26][CH:23]3[CH2:25][CH2:24]3)[C:5]=2[CH3:6])=[O:2])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 4

HCID 7757Methyl acetoacetateHCID 7965CyclohexylamineHCID 27568882-Bromo-1-(5-chloro-2-methoxy-4-methylphenyl)ethanoneHCID 10240761Cyclopropaneethanamine

Product 1

HCID 589990985-(5-Chloro-2-methoxy-4-methyl-phenyl)-1-(2-cyclopropyl-ethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide

Procedure

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-(5-chloro-2-methoxy-4-methyl-phenyl)-ethanone as compound of formula S, 2-cyclopropyl-ethylamine as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 429.6 (M+H)+.

Sources & evidence

ORD record
ord-d6abc013c10a42748a3e4e12febc2e3c
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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