2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid → 2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-[4-(2-oxo-2,3-dihydro-1,3-oxazol-5-yl)phenyl]butanamide

HRID 57001Notes

Reaction equation

HRID 57001 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17](O)=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:36][C:35](=[O:37])[NH:34][CH:33]=2)=[CH:28][CH:27]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]4[O:36][C:35](=[O:37])[NH:34][CH:33]=4)=[CH:30][CH:31]=3)=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 1176225692-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acidHCID 1176227935-(4-Aminophenyl)-1,3-oxazol-2(3H)-one

Product 1

HCID 1176229932-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-N-[4-(2-oxo-2,3-dihydro-1,3-oxazol-5-yl)phenyl]butanamide

Procedure

87 mg (0.25 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 60 mg (0.30 mmol, 1.2 eq.) of 5-(4-aminophenyl)-1,3-oxazol-2(3H)-one were reacted according to General Method 1. Yield: 23 mg (purity 93%, 17% of theory)

Sources & evidence

ORD record
ord-ff586029143a4e648ee797d507b2540d
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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