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

HRID 337169Notes

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-51e1cb9817664700991b9f8d3adfa63e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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