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With hydrogenchloride; In diethyl ether; at 20℃; for 2 - 3h;
Tert-butyl [2-(2 -methyl- lH-imidazol- 1 -yDethyl] carbamateSynthesis of hydrochloride salt of 2-(lH-imidazol-l-yl)ethanamine (Formula III) To the compound tert-butyl [2-(lH-imidazol-l-yl)ethyl]carbamate (2 g, 9.4 mmol) was added ethereal hydrochloric acid (15 ml) and stirred at room temperature for 2-3 hours. The solvent was evaporated under reduced pressure to furnish the title compound. Yield: 1.8g.
2-cyclopentyl-2-hydroxy-N-[2-(1H-imidazol-1-yl)ethyl]-2-phenylacetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Example 1 : Synthesis of 2-Cyclopentyl-2-hydroxy-lambda/-[2-(lH-imidazol-l-yl)ethyll-2- phenylacetamide (Compound No. 1) <n="36"/>To a solution of the hydrochloride salt of 2-(lH-imidazol-l-yl)ethanamine (0.5 g, 4.50 mmol) in chloroform (10 ml) was added N-methyl morpholine (2.96 ml, 27.02 mmol) and stirred the mixture for 5 to 10 minutes at the room temperature followed by the addition of 2- cyclopentyl-2-hydroxy-2-phenyl acetic acid (0.99 g, 4.5 mmol) and hydroxy benzotriazole (0.60 g, 4.5 mmol) at room temperature. The resulting reaction mixture was stirred for 30-45 minutes followed by the addition of l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and again stirred for over night. The mixture was diluted with water and stirred for 10-15 minutes followed by the addition of dichloromethane. The mixture was stirred for 15-20 minutes. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by preparative column chromatography using 10 % methanol in dichloromethane as eluent to furnish the title compound. Yield: 70 mg.1H NMR (CDCl3)delta: 7.60-7.31 (5H, m), 6.99 (IH, s), 6.99 (IH, s), 6.65 (IH, s), 4.01-4.00 (2H, m), 3.99-3.49 (2H, m), 3.11-3.07 (IH, m), 1.64-1.42 (8H, m).
5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxylic acid[ No CAS ]
N-(2-(1H-imidazol-1-yl)ethyl)-5,12-dioxo-5,12-dihydroindolizino[2,3-g]quinoline-6-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
42%
General procedure: At room temperature, to a red solution of compound 2 (150 mg,0.5 mmol) and triethylamine (0.14 mL, 1.0 mmol) in chloroform(40 mL), thionyl chloride (2.5 mL) was added dropwise. Themixture was stirred and heated under reflux for 5 h. The mixturegradually became a red solution. The reaction solution was then cooled to room temperature. The solvent was evaporated underreduced pressure. The residue was obtained under reduced pressurefor a period to get rid of most of the residual SOCl2 to give an orange solid residue. 4-(Dimethylamino)pyridine (70 mg,0.6 mmol) and different amine or alcohol derivative (1.80 mmol) inchloroform (30 mL) were added dropwise to the resultant residue.The reaction mixture instantaneously became a red solution. Thereaction mixture was heated under reflux for 5 h, and cooled toroom temperature. The solvent was evaporated under reducedpressure. The crude product was purified by silica gel columnchromatography to give the target compound.
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