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

HRID 56956Notes

Reaction equation

HRID 56956 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:33]#[N:34])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:31])[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:32])[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:33]#[N:34])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:31])[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:32])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622812tert-Butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate

Product 1

HCID 1176227374-({2-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoic acid

Procedure

43 mg (0.09 mmol) of tert-butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate (racemate) (Example 2.2C) were hydrolysed with TFA according to General Method 2. Yield: 20 mg (purity 89%, 48% of theory)

Sources & evidence

ORD record
ord-9919b5bdb2594e2fa3f2dc83553d2d36
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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