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CAS No.: | 56995-20-1 |
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Name: | Flupirtine |
Article Data: | 7 |
Molecular Structure: | |
Formula: | C15H17FN4O2 |
Molecular Weight: | 304.324 |
Synonyms: | Carbamicacid, [2-amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-, ethyl ester(9CI);D 9998;Flupirtine;Katadolon;Trancopal Dolo; |
EINECS: | 260-503-8 |
Density: | 1.35 g/cm3 |
Melting Point: | 115-116° |
Boiling Point: | 434.9 °C at 760 mmHg |
Flash Point: | 216.8 °C |
Solubility: | 1g/L(temperature not stated) |
PSA: | 89.27000 |
LogP: | 3.71060 |
chloroformic acid ethyl ester
N6-(4-fluorobenzyl)pyridine-2,3,6-triamine
Flupirtine
Conditions | Yield |
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In 1,4-dioxane at 20℃; Inert atmosphere; Darkness; | 82% |
In 1,4-dioxane at 20℃; for 1h; | 75% |
In tetrahydrofuran Ambient temperature; Yield given; |
2,3-Diaminopyridine
Flupirtine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 41.8 percent / propan-2-ol / 71 h / Heating 2: 52.8 percent / MnO2 / tetrahydrofuran / 18 h / Ambient temperature 3: Na2S2O4 / tetrahydrofuran; H2O / Ambient temperature 4: tetrahydrofuran / Ambient temperature View Scheme |
spiropyridine>
Flupirtine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 52.8 percent / MnO2 / tetrahydrofuran / 18 h / Ambient temperature 2: Na2S2O4 / tetrahydrofuran; H2O / Ambient temperature 3: tetrahydrofuran / Ambient temperature View Scheme |
5'-<(4-fluorobenzyl)amino>spiropyridine>
Flupirtine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: Na2S2O4 / tetrahydrofuran; H2O / Ambient temperature 2: tetrahydrofuran / Ambient temperature View Scheme |
2,6-dicholoro-3-nitropyridine
Flupirtine
Conditions | Yield |
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Multi-step reaction with 4 steps 1: ammonia / methanol / 20 °C / Inert atmosphere 2: triethylamine / isopropyl alcohol / 3 h / Reflux; Inert atmosphere 3: hydrogenchloride; tin(II) chloride dihdyrate / water / 3 h / 70 °C / Inert atmosphere 4: 1,4-dioxane / 20 °C / Inert atmosphere; Darkness View Scheme |
2-amino-6-chloro-3-nitropyridine
Flupirtine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / isopropyl alcohol / 3 h / Reflux; Inert atmosphere 2: hydrogenchloride; tin(II) chloride dihdyrate / water / 3 h / 70 °C / Inert atmosphere 3: 1,4-dioxane / 20 °C / Inert atmosphere; Darkness View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / isopropyl alcohol / 0.5 h / 5 °C 2: palladium on activated charcoal; hydrogen / methanol / 5 h / 20 °C / 1551.49 Torr 3: 1,4-dioxane / 1 h / 20 °C View Scheme |
2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine
Flupirtine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; tin(II) chloride dihdyrate / water / 3 h / 70 °C / Inert atmosphere 2: 1,4-dioxane / 20 °C / Inert atmosphere; Darkness View Scheme | |
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 5 h / 20 °C / 1551.49 Torr 2: 1,4-dioxane / 1 h / 20 °C View Scheme |
para-fluorobenzylamine
Flupirtine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / isopropyl alcohol / 0.5 h / 5 °C 2: palladium on activated charcoal; hydrogen / methanol / 5 h / 20 °C / 1551.49 Torr 3: 1,4-dioxane / 1 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
In Isopropyl acetate; dimethyl sulfoxide at 55℃; for 1h; Temperature; Solvent; Inert atmosphere; | 96% |
Flupirtine
Conditions | Yield |
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at 200℃; for 0.5h; | 88% |
The Flupirtine with CAS registry number of 56995-20-1 is also known as Flupirtinum. The IUPAC name is Ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamate. Its classification codes are Analgesics; Central Nervous System Agents; Peripheral Nervous System Agents; Sensory System Agents. In addition, the formula is C15H17FN4O2 and the molecular weight is 304.32.
Physical properties about Flupirtine are: (1)ACD/LogP: 1.46 ; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.35; (4)ACD/LogD (pH 7.4): 1.45; (5)ACD/BCF (pH 5.5): 5.88; (6)ACD/BCF (pH 7.4): 7.5; (7)ACD/KOC (pH 5.5): 115.33; (8)ACD/KOC (pH 7.4): 147.07; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 48.91Å2; (13)Index of Refraction: 1.661; (14)Molar Refractivity: 83.32 cm3; (15)Molar Volume: 225.2 cm3; (16)Polarizability: 33.03×10-24cm3; (17)Surface Tension: 60.6 dyne/cm; (18)Density: 1.35 g/cm3; (19)Flash Point: 216.8 °C ; (20)Enthalpy of Vaporization: 69.12 kJ/mol ; (21)Boiling Point: 434.9 °C at 760 mmHg ; (22)Vapour Pressure: 9.1E-08 mmHg at 25 °C.
Preparation of Flupirtine: it is prepared by reaction of 2-amino-3-nitro-6-chloro pyridine with p-fluorobenzyl amine. Then restore the resulting product, which is acylated by ethyl chloride. Finally, react with maleate in isopropyl alcohol to obtain the product.
Uses of Flupirtine: it is used as short-term treatment for surgery, trauma, burns and pain caused by toothache. What's more, it can act on the central nervous system without inhibition of respiration or cough.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCOC(=O)NC1=C(N=C(C=C1)NCC2=CC=C(C=C2)F)N
2. InChI: InChI=1S/C15H17FN4O2/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20)
3. InChIKey: JUUFBMODXQKSTD-UHFFFAOYSA-N