Methyl acetoacetate → 1-(Rac)-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-(2-fluoro-5-trifluoromethyl-phenyl)-2-methyl-1h-pyrrole-3-carboxylic acid ((1r,2r)-2-hydroxy-cyclohexyl)-amide

HRID 229873

Reaction equation

HRID 229873 reaction equation
CO[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].Br[CH2:10][C:11]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[F:23])=O.[CH3:24][C:25]1([CH3:32])[O:29][CH:28]([CH2:30][NH2:31])[CH2:27][O:26]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:10]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=2[F:23])[N:31]([CH2:30][CH:28]2[CH2:27][O:26][C:25]([CH3:32])([CH3:24])[O:29]2)[C:5]=1[CH3:6])=[O:8]

Participants

5

Reactant 4

HCID 7757Methyl acetoacetateHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27787842-Fluoro-5-(trifluoromethyl)phenacyl bromideHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-

Product 1

HCID 116562351-(Rac)-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-(2-fluoro-5-trifluoromethyl-phenyl)-2-methyl-1h-pyrrole-3-carboxylic acid ((1r,2r)-2-hydroxy-cyclohexyl)-amide

Procedure

The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-fluoro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, 2,2-dimethyl-1,3-dioxolan-4-methylamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH, MS (ISP) 499.5 (M+H)+.

Sources & evidence

ORD record
ord-263ddf3c7db74a4dafa89ecc3e47e864
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Linked notes

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