Methyl acetoacetate → 5-(2,5-Bis-trifluoromethyl-phenyl)-1-(2-cyclopropyl-ethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 2105819Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][C:5](=O)[CH3:6].[F:9][C:10]([F:26])([F:25])[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[C:21](=O)[CH2:22]Br.[CH:27]1([CH2:30][CH2:31][NH2:32])[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:22]=[C:21]([C:12]3[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=3[C:10]([F:26])([F:25])[F:9])[N:32]([CH2:31][CH2:30][CH:27]3[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 10240761Cyclopropaneethanamine

HCID 221379871-(2,5-Bis-trifluoromethyl-phenyl)-2-bromo-ethanone

Product 1

HCID 589989215-(2,5-Bis-trifluoromethyl-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, 1-(2,5-bis-trifluoromethyl-phenyl)-2-bromo-ethanone as compound of formula S, 2-cyclopropyl-ethylamine as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 487.4 (M+H)+.

Sources & evidence

ORD record: ord-53d2d084bd624d55a68deaf0c6484b41
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579369B2

Reaction notes

Loading…