Propargyl bromide → HCID 86755075, compound

HRID 849946Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=1[C:17]1[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:22]=1.[CH2:29](Br)[C:30]#[CH:31].[Cl-].[NH4+]>O1CCCC1>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([N:11]([CH2:31][C:30]#[CH:29])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=1[C:17]1[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][N:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Then, a mixture of 20 mg of sodium hydride (60% in oil) and 1.3 ml of tetrahydrofuran was cooled to 0° C. To this was added dropwise a solution of 0.21 g of 3-(2,4-dichloro-5-ethoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-346) in 1.3 ml of tetrahydrofuran. After stirring at 0° C. for 10 minutes, 42 μl of propargyl bromide was added, and the mixture was stirred at 0° C. for 1 hour. After completion of the reaction, the reaction mixture was poured into saturated ammonium chloride solution, followed by extraction with diethyl ether. The organic layer was dried with anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, which afforded 36 mg (yield, 16%) of 3-{2,4-dichloro-5-[N-(ethoxycarbonyl)propargylamino]phenyl}-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-351; m.p., 132.3° C.).

Workup

stirringthe mixture was stirred at 0° C. for 1 hour
customAfter completion of the reaction
extractionfollowed by extraction with diethyl ether
dry with materialThe organic layer was dried with anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-629db4fa92c14194a2a840f51626eaca
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015774

Reaction notes

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