Methyl acetoacetate → (s)-5-(3,5-Bis-trifluoromethyl-phenyl)-1-cyclopropylmethyl-2-methyl-1h-pyrrole-3-carboxylic acid sec-butylamide

HRID 1593158Notes

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.[CH:27]1([CH2:30][NH2:31])[CH2:29][CH2:28]1.[C@@H:32]([NH2:36])([CH2:34][CH3:35])[CH3:33]>>[C@@H:32]([NH:36][C:3]([C:4]1[CH:22]=[C:21]([C:13]2[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]=2)[N:31]([CH2:30][CH:27]2[CH2:29][CH2:28]2)[C:5]=1[CH3:6])=[O:2])([CH2:34][CH3:35])[CH3:33]

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 75646Cyclopropanemethanamine

HCID 27361703,5-Bis(trifluoromethyl)phenacyl bromide

HCID 67137532-Butanamine, (S)-

Product 1

HCID 58999102(s)-5-(3,5-Bis-trifluoromethyl-phenyl)-1-cyclopropylmethyl-2-methyl-1h-pyrrole-3-carboxylic acid sec-butylamide

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, cyclopropanemethylamine as R3—(CH2)m—NH2 and (S)-sec-butylamine as R1R2NH, MS (ISP) 447.3 (M+H)+.

Sources & evidence

ORD record: ord-b866a82195494e8bbbde42fa5411dd4e
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294644B2

Reaction notes

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