Trifluoroacetic acid → US10183932, Example 62

HRID 56995Notes

Reaction equation

HRID 56995 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:37]#[N:38])=[C:6]([C:8]2[C:13]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:12][N:11]([CH:18]([CH3:35])[C:19]([NH:21][C:22]3[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=[O:27])=[CH:24][CH:23]=3)=[O:20])[C:10](=[O:36])[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:37]#[N:38])=[C:6]([C:8]2[C:13]([O:14][CH:15]([CH3:16])[CH3:17])=[CH:12][N:11]([CH:18]([CH3:35])[C:19]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:33][CH:34]=3)=[O:20])[C:10](=[O:36])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622846tert-Butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-isopropoxy-2-oxopyridin-1(2H)-yl]propanoyl}amino)benzoate

Product 1

HCID 117622998US10183932, Example 62

Procedure

31 mg (0.06 mmol) of tert-butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-2-oxo-5-(propan-2-yloxy)pyridin-1(2H)-yl]propanoyl}amino)benzoate (racemate) (Example 24.11) were hydrolysed with TFA according to General Method 2. Yield: 5 mg (18% of theory)

Sources & evidence

ORD record
ord-d6a4e41acbc44a3691047555807b6c5a
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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