Pyruvic Acid → HCID 90039786, compound

HRID 526007Notes

Reaction equation

HRID 526007 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.N12CCN(CC1)CC2.[NH2:15][C:16]1[C:25](I)=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:27])[N:17]=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][O:22][C:20]([C:19]1[CH:24]=[C:25]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[NH:15][C:16]2=[N:17][C:18]=1[CH3:27])=[O:21]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 9237DabcoHCID 59747893HCID 59747893, compound

Product 1

HCID 90039786HCID 90039786, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under argon, pyruvic acid (6.90 ml, 100.1 mmol) and 1,4-diazabicyclo[2.2.2]octane (11.2 g, 100.1 mmol) were added to a solution of methyl 6-amino-5-iodo-2-methylnicotinate (9.00 g, 30.8 mmol) in N,N-dimethylformamide (88 ml), and the flask was evacuated and flushed with argon. Argon was subsequently passed through the solution for 5 min, palladium(II) acetate (0.345 g, 1.54 mmol) was then added and the mixture was heated at 100° C. for 2 h. The cooled solution was filtered through Celite and the dimethylformamide was distilled off. The residue was then taken up in water and acidified with hydrochloric acid, giving a solid (6.3 g, 86% of theory). HPLC-MS: log P=1.26; mass (m/z): 235.0 (M+H)+; 1H-NMR (DMSO) 2.79 (s, 3H), 3.85 (s, 3H), 7.19 (s, 1H), 8.62 (s, 1H), 12.50 (s, 1H).

Workup

  1. customthe flask was evacuated
  2. customflushed with argon
  3. filtrationThe cooled solution was filtered through Celite
  4. distillationthe dimethylformamide was distilled off
  5. customgiving a solid (6.3 g, 86% of theory)

Sources & evidence

ORD record
ord-9a619e9f2d914363960361d9b17d6462
Source dataset
uspto-grants-2016_05
Patent number
US09345247B2

Reaction notes

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