Dimethylformamide → HCID 14207358, compound

HRID 1647740Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH2:14][CH2:13]3)[CH:5]=[N:4][CH:3]=[N:2]1.CN(C=O)C.[H-].[Na+].[CH2:28](Br)[CH3:29]>O>[CH2:28]([N:16]1[C:17]2[C:12](=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:19][CH:18]=2)[CH2:13][CH2:14][C:15]1=[O:20])[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2 g (7.35 mM) of 6-[3-(1,2,4-triazol-1-yl)propoxy]-3,4-dihydrocarbostyril with 20 ml of DMF was added 350 mg (8.8 mM) of sodium hydride (60% in oil) and the mixture was heated at 60° C. for 30 minutes. Then under ice-cooling condition, 0.6 ml (8.1 mM) of ethyl bromide was added dropwise, further the reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water, then extracted with chloroform, the chloroform layer was washed with water, dried with anhydrous sodium sulfate, and concentrated by removing the solvent by evaporation. The resulting residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=30:1), then recrystallized from ethyl acetate-n-hexane to yield 1.8 g of 1-ethyl-6-[3-(1,2,4-triazol-1 -yl)propoxy]-3,4-dihydrocarbostyril. Colorless needle-like crystals. Melting point: 97.0°-98.0° C.

Workup

additionwas added dropwise
extractionextracted with chloroform
washthe chloroform layer was washed with water
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated
customby removing the solvent
customby evaporation
customThe resulting residue was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=30:1)
customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record: ord-abfc1b55cdf74bb49b9e79a459c21ef2
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05434164

Reaction notes

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