1236284-92-6 → tert-Butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)-2,5-difluorobenzoate

HRID 56931Notes

Reaction equation

HRID 56931 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[C:38]([F:39])=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[C:28]([F:40])[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[C:38]([F:39])=[CH:37][C:29]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[C:28]([F:40])[CH:27]=3)=[O:18])[C:10](=[O:22])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 580578441236284-92-6HCID 1176225692-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid

Product 1

HCID 117622601tert-Butyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)-2,5-difluorobenzoate

Procedure

150 mg (0.43 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 154 mg (0.61 mmol, 1.4 eq.) of tert-butyl 4-amino-2,5-difluorobenzoate were reacted according to General Method 5B. The crude product was purified by normal phase chromatography (mobile phase: cyclohexane/ethyl acetate 20-40% mixtures). Yield: 180 mg (71% of theory)

Workup

  1. customThe crude product was purified by normal phase chromatography (mobile phase: cyclohexane/ethyl acetate 20-40% mixtures)

Sources & evidence

ORD record
ord-a24a3c3a29744517b342b5000828855c
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

Loading…