Formic Acid → 5-[(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 1672608Notes

Reaction equation

HRID 1672608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([C:28]([NH:30][CH3:31])=[O:29])[C:13](=[O:27])[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[C:15]=2[CH3:16])=[CH:4][CH:3]=1.C(O)=[O:33]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:10]2[CH:11]=[C:12]([C:28]([NH:30][CH3:31])=[O:29])[C:13](=[O:27])[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[C:15]=2[CH3:16])=[O:33])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 673461225-[(4-chlorophenyl)ethynyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 673426465-[(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 66%

Conditions

Temperature
120 °C

Procedure

5-[(4-Chlorophenyl)ethynyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (111 mg, 0.25 mmol) was mixed with formic acid (1 ml) and heated in a microwave oven to 120° C. for 1 h. The formic acid was evaporated off and the residue was purified on an Xterra C8 column using a gradient of acetonitrile/water. Freeze drying of the mixture afforded 5-[(4-chlorophenyl)acetyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (77 mg, 66%).

Workup

  1. customThe formic acid was evaporated off
  2. customthe residue was purified on an Xterra C8 column
  3. customFreeze drying of the mixture

Sources & evidence

ORD record
ord-d3812bbbc44e4fb29ed1a66cc3241bd3
Source dataset
uspto-grants-2011_08
Patent number
US07998984B2

Reaction notes

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