Pyridine → HCID 22614844, compound

HRID 842658Notes

Reaction equation

HRID 842658 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][C:8]1[C:17]([Cl:18])=[C:16]([Cl: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[Cl: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 106066205-Amino-6,7-dichloro-2,3-dimethoxyquinoxaline

Product 1

HCID 22614844HCID 22614844, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methoxyacetylchloride (27.3 mL, 32.4 g, 0.30 mol) was added to a stirred mixture of 5-amino-6,7-dichloro-2,3-dimethoxyquinoxaline (Preparation 26, 73.8 g, 0.27 mol) and pyridine (26.4 mL, 25.8 g, 0.33 mol) in dichloromethane (1.2L) at room temperature under nitrogen. After 18 hours stirring at room temperature, the mixture was washed with 2M aqueous hydrochloric acid solution followed by brine, then dried (MgSO4) and concentrated under reduced pressure. The residue was triturated with methanol and filtered to give 6,7-dichloro-2,3-dimethoxy-5-methoxyacetamidoquinoxaline (82.0 g, 88%) as an off-white solid, mp 171-173° C.

Workup

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

Sources & evidence

ORD record
ord-533406f402aa42f081a7f36dcedee4a4
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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