Pyridine → HCID 22614853, compound

HRID 842691Notes

Reaction equation

HRID 842691 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][C:8]1[C:17]([Cl:18])=[C:16]([CH3:19])[CH:15]=[C:14]2[C:9]=1[N:10]=[C:11]([O:22][CH3:23])[C:12]([O:20][CH3:21])=[N:13]2.N1C=CC=CC=1>ClCCl>[Cl:18][C:17]1[C:8]([NH:7][C:4](=[O:5])[CH2:3][O:2][CH3:1])=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:19])[N:13]=[C:12]([O:20][CH3:21])[C:11]([O:22][CH3:23])=[N:10]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 22614878HCID 22614878, compound

Product 1

HCID 22614853HCID 22614853, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methoxyacetylchloride (2.16 mL, 2.57 g, 23.66 mmol) was added to a solution of 5-amino-6-chloro-2,3-dimethoxy-7-methylquinoxaline (Preparation 113, 5 g, 19.72 mmol) and pyridine (1.91 mL, 1.89 g, 23.66 mmol) in dichloromethane (80 mL) at 0° C. After a further 1 hour at this temperature, the mixture was washed with 2M aqueous hydrochloric acid solution, brine, dried (MgSO4) and concentrated under reduced pressure. The residue was triturated with diisopropyl ether and filtered to give 6-chloro-2,3-dimethoxy-5-methoxyacetamido-7-methylquinoxaline (6.06 g, 98%) as an off white solid, mp 170-171° C.

Workup

  1. washthe mixture was washed with 2M aqueous hydrochloric acid solution, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with diisopropyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-602df7bdd4d54577a584720e96664047
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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