Trifluoroacetic acid → 4-({2-[5-Chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoic acid

HRID 56977Notes

Reaction equation

HRID 56977 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=2[C:34]#[N:35])=[CH:4][C:5](=[O:26])[N:6]([CH:8]([CH3:25])[C:9]([NH:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:14][CH:13]=2)=[O:10])[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[C:3]([C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=2[C:34]#[N:35])=[CH:4][C:5](=[O:26])[N:6]([CH:8]([CH3:25])[C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:23][CH:24]=2)=[O:10])[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622701tert-Butyl 4-({2-[5-chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate

Product 1

HCID 1176226904-({2-[5-Chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoic acid

Procedure

281 mg (purity 58%, 0.32 mmol) of tert-butyl 4-({2-[5-chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate (racemate) (Example 12.1E) were hydrolysed with TFA according to General Method 2. Yield: 97 mg (67% of theory)

Sources & evidence

ORD record
ord-9413f70ca3b5442d83338ce432f44264
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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