Trifluoroacetic acid → methyl 4-chloro-3-(2,3-dioxo-3,4-dihydropyrazin-1(2H)-yl)benzoate

HRID 1697427Notes

Reaction equation

HRID 1697427 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][C:13](=[O:23])[C:14]([NH:16][CH2:17][CH:18](OC)OC)=[O:15].FC(F)(F)C(O)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:18]=[CH:17][NH:16][C:14](=[O:15])[C:13]1=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66688946Methyl 4-chloro-3-{[[(2,2-dimethoxyethyl)amino](oxo)acetyl]amino}benzoate

Product 1

HCID 66690376methyl 4-chloro-3-(2,3-dioxo-3,4-dihydropyrazin-1(2H)-yl)benzoateYield 115.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of methyl 4-chloro-3-{[[(2,2-dimethoxyethyl)amino](oxo)acetyl]amino}benzoate (Example 330c, 8.5 g) in acetic acid (26 mL) was treated with trifluoroacetic acid (8.5 mL) under nitrogen. The resulting mixture was stirred at 120° C. for 3 h. The mixture was quenched with water (20 mL) and the resulting solid filtered off to give the subtitle compound (8.00 g).

Workup

  1. customThe mixture was quenched with water (20 mL)
  2. filtrationthe resulting solid filtered off

Sources & evidence

ORD record
ord-fc21d3d5c1724fa981a546fe9375f826
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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