2-Bromopropionic acid → 2-[4-(5-Chloro-2-cyanophenyl)-5-ethoxy-2-oxopyridin-1(2H)-yl]propanoic acid

HRID 56853Notes

Reaction equation

HRID 56853 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([O:16][CH2:17][CH3:18])=[CH:14][NH:13][C:12](=[O:19])[CH:11]=2)[CH:3]=1.Br[CH:21]([CH3:25])[C:22]([OH:24])=[O:23]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([O:16][CH2:17][CH3:18])=[CH:14][N:13]([CH:21]([CH3:25])[C:22]([OH:24])=[O:23])[C:12](=[O:19])[CH:11]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 117292-Bromopropionic acidHCID 1176054644-Chloro-2-(5-ethoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile

Product 1

HCID 1176227102-[4-(5-Chloro-2-cyanophenyl)-5-ethoxy-2-oxopyridin-1(2H)-yl]propanoic acid

Procedure

134 mg (0.37 mmol) of 4-chloro-2-(5-ethoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile and 1.5 eq. of 2-bromopropanoic acid (racemate) were reacted according to General Method 4A at 50° C. The crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 89 mg (purity 86%, 60% of theory)

Workup

  1. customaccording to General Method 4A at 50° C
  2. customThe crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-420733b409d34eadada938daae507e3e
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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