N-(2-ethoxy) feriilamidoethyl nitrate compound and preparation method thereof
A kind of technology of ferulic acid amide, nitrate is applied in the present invention to provide a kind of N-ferulic amide nitrate compound represented by general formula, 0005] aiming at the upper field of prior art
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0034] Example 1.2-Methoxy-4-(3-(2-(nitrooxy)ethylamine)-3-oxopropen-1-yl)phenyl 3-(diethylamino)propionate salt salt synthesis
[0035] (1) Synthesis of 2-aminoethyl nitrate nitrate
[0036]
[0037] Add fuming HNO to a 2L three-neck round bottom flask 3 (259g, 4.1mol), add acetic anhydride (668g, 6.6mol) dropwise at -20°C for 1 hour, then add 2-aminoethanol (50g, 0.8mol) in 650mL of acetic acid dropwise at -20°C ethyl ester solution. The above mixture was stirred at -20°C for 1 hour, and 900 mL of n-hexane was added. The mixture was filtered to obtain 2-aminoethyl nitrate nitrate as a white solid (105 g, yield 76%).
[0038] (2) Synthesis of (2-(3-(4-hydroxy-3-methoxy)phenyl)acrylamide)ethyl nitrate
[0039]
[0040] Add 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (168.2g, 0.87mol), 2-aminoethyl nitrate (153.6g, 0.91mol) and N at 0°C for 1 hour, To a mixture of N-lutylpyridin-4-amine (105.6 g, 0.87 mol) in 4000 mL of dichloromethane was added EDC (173.6 g, 0.91 mol...
Embodiment 2
[0055](1) Synthesis of 2-methoxy-4-(3-(2-(nitrooxy)ethylamino)-3-oxopropen-1-yl)phenyl 3-morpholine propionate
[0056]
[0057] At -30°C, 2-methoxy-4-(3-(2-(nitrooxy)ethylamino)-3-oxopropen-1-yl)phenyl-3-bromopropyl To a solution of ester (9.8 g, 0.024 mol) in 400 mL of dichloromethane and 20 mL of THF was added morpholine (4.9 g, 0.56 mol). The mixture was warmed to room temperature and stirred for 18h. The mixture was filtered and concentrated. The residue was washed with ether to give 2-methoxy-4-(3-(2-(nitrooxy)ethylamino)-3-oxopropen-1-yl)phenyl 3-morpholine propionate pink Solid (9 g, 72% yield).
[0058] (2) 2-methoxy-4-(3-(2-(nitrooxy)ethylamino)-3-oxopropen-1-yl)phenyl 3-morpholine propionate hydrochloride synthesis
[0059]
[0060] 2-methoxy-4-(3-(2-(nitrooxy)ethylamino)-3-oxopropen-1-yl)phenyl 3-morpholine propionate (8.9g, 0.021mol) of 400mL of dichloromethane and 100mL of THF was passed through HCl (gas) for 1 hour. The mixture was filtered, washed ...
Embodiment 3
[0063] (1) Synthesis of tetrahydro-2H-pyran-4-carbonyl chloride
[0064]
[0065] In a 100ml round-bottomed flask equipped with a reflux condenser, add 40mL of a solution of tetrahydro-2H-pyran-4-carboxylic acid (5.0g, 0.038mol) in thionyl chloride. DMF (2 drops) was added and the mixture was stirred at 78°C for 18 hours. The mixture was concentrated under reduced pressure to give tetrahydro-2H-pyran-4-carbonyl chloride (5.44 g, 95.6%) as a yellow oil, which was used directly in the next step without purification.
[0066] (2) 2-methoxy-4-(3-(2-(nitrooxy)ethylamino)-3-oxopropen-1-yl)phenyltetrahydro-2H-pyran-4-carboxy Synthesis of esters
[0067]
[0068] To a solution of 2-(3-(4-hydroxy-3-methoxyphenyl)acrylamide)ethyl nitrate (8.0 g, 0.283 mol) in 100 mL THF at room temperature was added tetrahydro-2H-pyridine Pyran-4-carbonyl chloride (5.44g, 0.37mol), the mixture was cooled to -30°C, a solution of pyridine (2.46g, 0.0311mol) dissolved in 20mL of dichloromethane wa...
PUM
| Property | Measurement | Unit |
|---|---|---|
| wavelength | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to View More