Methyl acetoacetate → 5-(2-Chloro-5-trifluoromethyl-phenyl)-1-((1RS,2RS)-2-hydroxy-cyclohexylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 2105823Notes

Reaction equation

HRID 2105823 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]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[Cl:23])=O.[NH2:24][CH2:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[OH:32].[CH:33]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:33]1([NH:39][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:24]([CH2:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]3[OH:32])[C:5]=2[CH3:6])=[O:2])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 4

HCID 7757Methyl acetoacetateHCID 7965CyclohexylamineHCID 2724658trans-2-Aminomethyl-1-cyclohexanolHCID 27831832-Chloro-5-(trifluoromethyl)phenacyl bromide

Product 1

HCID 100745765-(2-Chloro-5-trifluoromethyl-phenyl)-1-((1RS,2RS)-2-hydroxy-cyclohexylmethyl)-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-(2-chloro-5-trifluoromethyl-phenyl)-ethanone as compound of formula S, trans-2-aminomethyl-1-cyclohexanol as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 497.4 (M+H)+.

Sources & evidence

ORD record
ord-3dbd931665e24415ba71013a346b834b
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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