Methyl acetoacetate → 5-(5-Chloro-2-fluoro-phenyl)-1-cyclopropylmethyl-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 2105817Notes

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

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 7965Cyclohexylamine

HCID 75646Cyclopropanemethanamine

HCID 790219212-Bromo-1-(5-chloro-2-fluorophenyl)ethanone

Product 1

HCID 589991515-(5-Chloro-2-fluoro-phenyl)-1-cyclopropylmethyl-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-fluoro-phenyl)-ethanone as compound of formula S, cyclopropanemethylamine as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 389.3 (M+H)+.

Sources & evidence

ORD record: ord-64f346f3d4004ed48b52d8da6db3e1b5
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579369B2

Reaction notes

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