Ethyl Acetate → 3-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-benzyloxycarbonylmethyl-pyrazinone

HRID 322544Notes

Reaction equation

HRID 322544 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][N:12]1[C:17]([CH3:18])=[C:16]([Cl:19])[N:15]=[C:14](Cl)[C:13]1=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C[CH2:33][O:34]C(C)=O>>[CH3:33][O:34][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:14]2[C:13](=[O:21])[N:12]([CH2:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[C:17]([CH3:18])=[C:16]([Cl:19])[N:15]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 11815413Benzyl(methoxy)amine

Product 1

HCID 220087883-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-benzyloxycarbonylmethyl-pyrazinone

Procedure

A solution of the pyrazinone 18-3 (5 g, 15.3 mmol) and 4 methoxybenzylamine (6.0 mL, 45.9 mmol) in EtOAc (60 mL) was heated at 80° C. for 2 h. The solution was cooled and filtered. The filtrate was concentrated in vacuo, the residue swished with MeOH and filtered to afford the title compound as a solid:

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0cb39b0ab66c464c93d83929b0883b8c
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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