Trifluoroacetic acid → 4-{[2-{4-[5-Chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}-3-(pyridin-3-yl)propanoyl]amino}benzoic acid

HRID 56972Notes

Reaction equation

HRID 56972 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]([F:42])([F:41])[F:40])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[C:15]([NH:17][C:18]3[CH:30]=[CH:29][C:21]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:20][CH:19]=3)=[O:16])[C:10](=[O:38])[CH:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:39]([F:42])([F:40])[F:41])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:29][CH:30]=3)=[O:16])[C:10](=[O:38])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622696tert-Butyl 4-{[2-{4-[5-chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}-3-(pyridin-3-yl)propanoyl]amino}benzoate

Product 1

HCID 1176226124-{[2-{4-[5-Chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}-3-(pyridin-3-yl)propanoyl]amino}benzoic acid

Procedure

33 mg (purity 94%, 0.05 mmol) of tert-butyl 4-{[2-{4-[5-chloro-2-(trifluoromethyl)phenyl]-2-oxopyridin-1(2H)-yl}-3-(pyridin-3-yl)propanoyl]amino}benzoate (racemate) (Example 9.1C) were hydrolysed with TFA according to General Method 2. Yield: 11 mg (40% of theory)

Sources & evidence

ORD record
ord-e37047f1774b488c9f8550a333576efe
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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