4-(1,2,4-Oxadiazol-3-yl)aniline → HCID 117623031, compound

HRID 57071Notes

Reaction equation

HRID 57071 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.[O:25]1[CH:29]=[N:28][C:27]([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)=[N:26]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:34][C:33]3[CH:32]=[CH:31][C:30]([C:27]4[N:28]=[CH:29][O:25][N:26]=4)=[CH:36][CH:35]=3)=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 214837044-(1,2,4-Oxadiazol-3-yl)anilineHCID 1176225692-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid

Product 1

HCID 117623031HCID 117623031, compound

Procedure

100 mg (0.29 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 73 mg (0.43 mmol, 1.5 eq.) of 4-(1,2,4-oxadiazol-3-yl)aniline were reacted according to General Method 7. The crude product was purified by normal phase chromatography (mobile phase: dichloromethane/methanol 2-5% mixtures) and subsequently by preparative HPLC (water/acetonitrile/0.1% formic acid gradient). Yield: 81 mg (55% of theory)

Workup

  1. customThe crude product was purified by normal phase chromatography (mobile phase: dichloromethane/methanol 2-5% mixtures) and subsequently by preparative HPLC (water/acetonitrile/0.1% formic acid gradient)

Sources & evidence

ORD record
ord-aeb845fab80d4b8ab7544b8f79c57a13
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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