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

HRID 56970Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622699tert-Butyl 4-[(2-{4-[5-chloro-2-(trifluoromethoxy)phenyl]-2-oxopyridin-1(2H)-yl}-3-cyclopropylpropanoyl)amino]benzoate

Product 1

HCID 862975424-[(2-{4-[5-Chloro-2-(trifluoromethoxy)phenyl]-2-oxopyridin-1(2H)-yl}-3-cyclopropylpropanoyl)-amino]benzoic acid

Procedure

77 mg (purity 92%, 0.12 mmol) of tert-butyl 4-[(2-{4-[5-chloro-2-(trifluoromethoxy)phenyl]-2-oxopyridin-1(2H)-yl}-3-cyclopropylpropanoyl)amino]benzoate (racemate) (Example 6.2C) were hydrolysed with TFA according to General Method 2. Yield: 41 mg (64% of theory)

Sources & evidence

ORD record: ord-48746e79e4df4ef4880a9b1c2442eff1
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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