2-(4-Fluorophenyl)-2-oxoacetic Acid → (S)-2-(4-Fluoro-phenyl)-2-hydroxy-N-(3-methyl-1H-indazol-5-yl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094443

Reaction equation

HRID 1094443 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17]([CH2:20][C:21]#N)=[CH:16][CH:15]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:36])[C:33](O)=[O:34])=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:27]=[CH:28][C:29]([C@H:32]([OH:36])[C:33]([N:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])[CH2:21][CH2:20][C:17]2[CH:18]=[N:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)=[O:34])=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 5794402-(4-Fluorophenyl)-2-oxoacetic AcidHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-HCID 178434299HCID 178434299, compound

Product 1

HCID 178434301(S)-2-(4-Fluoro-phenyl)-2-hydroxy-N-(3-methyl-1H-indazol-5-yl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Procedure

In analogy to example 47, 3-Methyl-1H-indazol-5-ylamine, (6-Trifluoromethyl-pyridin-3-yl)-acetonitrile & (4-fluoro-phenyl)-oxo-acetic acid were successively coupled then reduced to give after silica gel and chiral chromatography the target compound. MS(m/e): 473.1 [M+H]+.

Workup

  1. customto give after silica gel and chiral chromatography the target compound

Sources & evidence

ORD record
ord-5771199981f34e7a965c33497b8433a4
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Linked notes

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