Benzoic acid, 4-amino-, 1,1-dimethylethyl ester → tert-Butyl 4-{[2-(4-bromo-5-cyano-2-oxopyridin-1(2H)-yl)propanoyl]amino}benzoate

HRID 56722Notes

Reaction equation

HRID 56722 reaction equation
[Br:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]([CH:10]([CH3:14])[C:11]([OH:13])=O)[C:4](=[O:15])[CH:3]=1.[NH2:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=1>>[Br:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]([CH:10]([CH3:14])[C:11]([NH:16][C:17]2[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[CH:19][CH:18]=2)=[O:13])[C:4](=[O:15])[CH:3]=1

Participants

3

Reactant 2

HCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 1176226522-(4-Bromo-5-cyano-2-oxopyridin-1(2H)-yl)propanoic acid

Product 1

HCID 117622561tert-Butyl 4-{[2-(4-bromo-5-cyano-2-oxopyridin-1(2H)-yl)propanoyl]amino}benzoate

Procedure

750 mg (purity 70%, 1.94 mmol) of 2-(4-bromo-5-cyano-2-oxopyridin-1(2H)-yl)propanoic acid (racemate) and 1.2 eq. of tert-butyl 4-aminobenzoate were reacted according to General Method 5A. Yield: 704 mg (purity 70%, 57% of theory)

Sources & evidence

ORD record
ord-0665e656cc074ad2a41270956a753cb4
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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