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

HRID 1593144Notes

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].[C@H:36]([NH2:40])([CH2:38][CH3:39])[CH3:37]>>[C@H:36]([NH:40][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:32]([CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[C:28]([F:27])[CH:29]=2)[C:5]=1[CH3:6])=[O:2])([CH2:38][CH3:39])[CH3:37]

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 668533-Fluorobenzylamine

HCID 2724537(R)-sec-butylamine

HCID 27361703,5-Bis(trifluoromethyl)phenacyl bromide

Product 1

HCID 58999076(r)-5-(3,5-Bis-trifluoromethyl-phenyl)-1-(3-fluoro-benzyl)-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, 3-fluorobenzylamine as R3—(CH2)m—NH2 and (R)-sec-butylamine as R1R2NH, MS (ISP) 501.2 (M+H)+.

Sources & evidence

ORD record: ord-1c428d04cb30408e905d7e51eee89ab9
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294644B2

Reaction notes

Loading…