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

HRID 229870

Reaction equation

HRID 229870 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.[CH2:24]([NH2:30])[C@@H:25]1[O:29][CH2:28][CH2:27][CH2:26]1.[CH:31]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH:31]1([NH:37][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:30]([CH2:24][C@H:25]3[CH2:26][CH2:27][CH2:28][O:29]3)[C:5]=2[CH3:6])=[O:2])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 4

HCID 7757Methyl acetoacetateHCID 7965CyclohexylamineHCID 2734124(R)-(-)-TetrahydrofurfurylamineHCID 27787842-Fluoro-5-(trifluoromethyl)phenacyl bromide

Product 1

HCID 117193935-(2-Fluoro-5-trifluoromethyl-phenyl)-2-methyl-1-[(R)-1-(tetrahydro-furan-2-yl)methyl]-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, (R)-tetrahydrofurfurylamine as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 453.6 (M+H)+.

Sources & evidence

ORD record
ord-9d94c12581484394aed0c0f6b34f563a
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Linked notes

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