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

HRID 2070849Notes

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

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

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

Sources & evidence

ORD record: ord-7aa11dac019b4237b53620a523de41eb
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299246B2

Reaction notes

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