2-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acid → 2-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-{4-[3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]phenyl}propanamide

HRID 56949Notes

Reaction equation

HRID 56949 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]#[N:21])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:18])[C:15]([OH:17])=O)[C:10](=[O:19])[CH:9]=2)[CH:7]=1.[F:22][C:23]([F:37])([F:36])[C:24]1[N:28]=[C:27]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[NH:26][N:25]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]#[N:21])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH3:18])[C:15]([NH:33][C:32]3[CH:34]=[CH:35][C:29]([C:27]4[NH:26][N:25]=[C:24]([C:23]([F:37])([F:36])[F:22])[N:28]=4)=[CH:30][CH:31]=3)=[O:17])[C:10](=[O:19])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 1176228502-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acidHCID 178507445HCID 178507445, compound

Product 1

HCID 1784600122-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-{4-[3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]phenyl}propanamide

Procedure

95 mg (purity 83%, 0.26 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acid (racemate) (Example 2.2B) and 75 mg (0.31 mmol) of 4-[3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]aniline (Example 1.1C) were reacted according to General Method 1. Yield: 30 mg (purity 92%, 21% of theory)

Sources & evidence

ORD record
ord-cd78eead7be64c7aa1dc6697511c6382
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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