Trifluoroacetic acid → 4-({2-[4-(2-Bromo-5-chlorophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoic acid

HRID 57028Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[C:14]([O:15][CH3:16])=[CH:13][N:12]([CH:17]([CH3:34])[C:18]([NH:20][C:21]2[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:23][CH:22]=2)=[O:19])[C:11](=[O:35])[CH:10]=1.C(O)(C(F)(F)F)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[C:14]([O:15][CH3:16])=[CH:13][N:12]([CH:17]([CH3:34])[C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:32][CH:33]=2)=[O:19])[C:11](=[O:35])[CH:10]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117622595tert-Butyl 4-({2-[4-(2-bromo-5-chlorophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate

Product 1

HCID 862979514-({2-[4-(2-Bromo-5-chlorophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoic acid

Procedure

72 mg (purity 73%, 0.09 mmol) of tert-butyl 4-({2-[4-(2-bromo-5-chlorophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate (racemate) were hydrolysed with TFA according to General Method 2. Yield: 20 mg (42% of theory)

Sources & evidence

ORD record: ord-915c93bbb443488e8dd63d5f5feb59da
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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