Methyl acetoacetate → 5-(2-Fluoro-5-trifluoromethyl-phenyl)-2-methyl-1-[2-(tetrahydro-pyran-4-yl)-ethyl]-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 229867

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[F:23])=O.[NH2:24][CH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[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[F:23])[N:24]([CH2:25][CH2:26][CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[C:5]=2[CH3:6])=[O:2])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 7965Cyclohexylamine

HCID 27731982-(Oxan-4-yl)ethan-1-amine

HCID 27787842-Fluoro-5-(trifluoromethyl)phenacyl bromide

Product 1

HCID 116701945-(2-Fluoro-5-trifluoromethyl-phenyl)-2-methyl-1-[2-(tetrahydro-pyran-4-yl)-ethyl]-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-fluoro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, 4-(2-aminoethyl)-tetrahydropyrane as R3—(CH2)m—NH2 and 1-cyclohexylamine as R1R2NH, MS (ISP) 481.6 (M+H)+.

Sources & evidence

ORD record: ord-160b7fc496ff49f9bcfcc6341de018a7
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563910B2

Linked notes

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