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-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]propanamide

HRID 56955Notes

Reaction equation

HRID 56955 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.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[NH:33][C:32](=[O:34])[O:31][N:30]=2)=[CH:25][CH:24]=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:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]4[NH:33][C:32](=[O:34])[O:31][N:30]=4)=[CH:27][CH:28]=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 1354531853-(4-Aminophenyl)-1,2,4-oxadiazol-5(2H)-one

Product 1

HCID 1369302412-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]-N-[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]propanamide

Procedure

120 mg (purity 93%, 0.37 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acid (racemate) (Example 2.2B) and 1.2 eq. of 3-(4-aminophenyl)-1,2,4-oxadiazol-5(4H)-one (Example 1.5A) were reacted according to General Method 1. Yield: 23 mg (13% of theory)

Sources & evidence

ORD record
ord-d4b0f41bd5c648019ef0b382539e6e17
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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