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

HRID 2105812Notes

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][NH2:31])[CH2:29][CH2:28]1.[CH:32]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([NH:38][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:31]([CH2:30][CH:27]3[CH2:29][CH2:28]3)[C:5]=2[CH3:6])=[O:2])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 7965Cyclohexylamine

HCID 75646Cyclopropanemethanamine

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

Product 1

HCID 589989495-(2,5-Bis-trifluoromethyl-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, 1-(2,5-bis-trifluoromethyl-phenyl)-2-bromo-ethanone as compound of formula S, cyclopropanemethylamine as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 473.1 (M+H)+.

Sources & evidence

ORD record: ord-b2d5b4b7d0c945bcb0874e8e738a1614
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579369B2

Reaction notes

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