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

HRID 2105820Notes

Reaction equation

CO[C:3](=[O:8])[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.[NH2:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@H:35]1[OH:40]>>[OH:40][C@@H:35]1[CH2:36][CH2:37][CH2:38][CH2:39][C@H:34]1[NH:33][C:3]([C:4]1[CH:22]=[C:21]([C:12]2[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=2[C:10]([F:26])([F:25])[F:9])[N:32]([CH2:31][CH2:30][CH:27]2[CH2:29][CH2:28]2)[C:5]=1[CH3:6])=[O:8]

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 735777(1R,2R)-2-Aminocyclohexanol

HCID 10240761Cyclopropaneethanamine

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

Product 1

HCID 102554875-(2,5-Bis-trifluoromethyl-phenyl)-1-(2-cyclopropyl-ethyl)-2-methyl-1H-pyrrole-3-carboxylic acid ((1R,2R)-2-hydroxy-cyclohexyl)-amide

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 (1R,2R)-2-amino-cyclohexanol as R1R2NH, MS (ISP) 503.1 (M+H)+.

Sources & evidence

ORD record: ord-afc1a13082a6435da3e962bbfa51e6b5
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579369B2

Reaction notes

Loading…