Dimethylformamide → HCID 18408334, compound

HRID 992882Notes

Reaction equation

CN(C=O)C.[F:6][C:7]1[C:16]([C:17]2[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)=[CH:15][C:10]2[NH:11][C:12](=[O:14])[S:13][C:9]=2[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[C:36]#[CH:37]>O>[F:6][C:7]1[C:16]([C:17]2[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)=[CH:15][C:10]2[N:11]([CH2:37][C:36]#[CH:35])[C:12](=[O:14])[S:13][C:9]=2[CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 10 ml of DMF, 0.4 g (1.2 mmol) of 3-(6-fluoro-benzothiazolin-2-on-5-yl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone, 0.18 g (1.3 mmol) of potassium carbonate and 0.15 g (1.3 mmol) of propargyl bromide were added, followed by heating and stirring at 70° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.32 g (yield: 72%) of the desired product. Melting point: 150-151° C.

Workup

temperatureby heating
customAfter completion of the reaction
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThe organic layer was distilled off under reduced pressure
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ec9383b38ca64f98b97d10365cf9e008
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472348B1

Reaction notes

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