Water → HCID 19365484, compound

HRID 849932Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:12]3[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:17]=3)[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]#[CH:32].O>CN(C)C=O>[O:1]=[C:2]1[N:7]([CH2:32][C:31]#[CH:30])[C:6]2[CH:8]=[C:9]([C:12]3[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:17]=3)[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

Then, 0.15 g of 3-(3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 2-1) was dissolved in 0.92 ml of N,N-dimethylformamide, to which 0.127 g of potassium carbonate and 70 μl of propargyl bromide were added, and the mixture was stirred at 60° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 0.12 g (yield, 74%) of 3-(3-oxo-4-propargyl-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 2-13; m.p., 129.2° C.).

Workup

additionwere added
customAfter completion of the reaction
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated sodium chloride solution
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-33024f35f8544357a63dc384d2a267f7
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015774

Reaction notes

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