2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid → HCID 178454445, compound

HRID 57069Notes

Reaction equation

HRID 57069 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[NH:36][C:35](=[S:37])[O:34][N: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[NH:36][C:35](=[S:37])[O:34][N: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 178507476HCID 178507476, compound

Product 1

HCID 178454445HCID 178454445, compound

Procedure

36 mg (0.10 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 30 mg (0.16 mmol, 1.5 eq.) of 3-(4-aminophenyl)-1,2,4-oxadiazole-5(4H)-thione were reacted according to General Method 7. The crude product was purified by preparative HPLC (water/acetonitrile/0.1% formic acid gradient). Yield: 21 mg (38% of theory)

Workup

  1. customThe crude product was purified by preparative HPLC (water/acetonitrile/0.1% formic acid gradient)

Sources & evidence

ORD record
ord-11925017918f4880b9dd04c10cf8b910
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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