Pyridine → HCID 58532501, compound

HRID 1846271Notes

Reaction equation

HRID 1846271 reaction equation
Cl[C:2]([C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][C:12](=[O:14])[CH3:13])=[C:6]([CH3:15])[CH:5]=1)=[O:3].[NH2:16][C:17]1[C:22]([C:23](O)=[O:24])=[CH:21][N:20]=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:10][C:8]1[CH:9]=[C:4]([C:2]2[O:3][C:23](=[O:24])[C:22]3[CH:21]=[N:20][CH:19]=[CH:18][C:17]=3[N:16]=2)[CH:5]=[C:6]([CH3:15])[C:7]=1[O:11][C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3199794-Aminonicotinic acidHCID 18704177Acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester

Product 1

HCID 58532501HCID 58532501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetic acid 4-chlorocarbonyl-2,6-dimethylphenyl ester (2.32 g, 10.0 mmol) in anhydrous CH2Cl2 (30 mL) were added 4-amino-nicotinic acid (4) (1.10 g, 8.00 mmol) and pyridine (2.37 g, 30.0 mmol). The reaction mixture was stirred at room temperature under nitrogen for 40 hours. Solvent was evaporated. The residue was diluted with methanol (20 mL). The solid separated was filtered, washed with methanol (2×10 mL) and dried under vacuum to give acetic acid 2,6-dimethyl-4-(4-oxo-4H-pyrido[4,3-d][1,3]oxazin-2-yl)-phenyl ester (6) as yellow solid. Yield: 1.99 g (64%).

Workup

  1. customSolvent was evaporated
  2. additionThe residue was diluted with methanol (20 mL)
  3. customThe solid separated
  4. filtrationwas filtered
  5. washwashed with methanol (2×10 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c6e0145416094ea58a248c2060c9ff17
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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