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

HRID 2105772Notes

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:12]=[C:13]([C:21](=O)[CH2:22]Br)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32].[CH:36]1([NH2:42])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>>[CH:36]1([NH:42][C:3]([C:4]2[CH:22]=[C:21]([C:13]3[CH:12]=[C:11]([C:10]([F:26])([F:25])[F:9])[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=3)[N:32]([CH2:31][C:30]3[CH:33]=[CH:34][CH:35]=[C:28]([F:27])[CH:29]=3)[C:5]=2[CH3:6])=[O:2])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 7965Cyclohexylamine

HCID 668533-Fluorobenzylamine

HCID 27361703,5-Bis(trifluoromethyl)phenacyl bromide

Product 1

HCID 589989635-(3,5-Bis-trifluoromethyl-phenyl)-1-(3-fluoro-benzyl)-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-(3,5-bis-trifluoromethyl-phenyl)-2-bromo-ethanone as compound of formula S, 3-fluorobenzylamine as R3-(CH2)m-NH2 and cyclohexylamine as R1R2NH, MS (ISP) 527.2 (M+H)+.

Sources & evidence

ORD record: ord-31c924e2f8a445ee86284ab8ab84e9f6
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579369B2

Reaction notes

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