Flupirtine supplier | CasNO.56995-20-1

Name
Flupirtine
EINECS 260-503-8
CAS No. 56995-20-1
Article Data7
CAS DataBase
Density 1.35 g/cm³
Solubility 1g/L(temperature not stated)
Melting Point 115-116°
Formula C₁₅H₁₇FN₄O₂
Boiling Point 434.9 °C at 760 mmHg
Molecular Weight 304.324
Flash Point 216.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Carbamicacid, [2-amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-, ethyl ester(9CI);D 9998;Flupirtine;Katadolon;Trancopal Dolo;
PSA 89.27000
LogP 3.71060

Synthetic route

: 541-41-3
chloroformic acid ethyl ester

: 112523-78-1
N6-(4-fluorobenzyl)pyridine-2,3,6-triamine

: 56995-20-1
Flupirtine

Conditions

Conditions	Yield
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;

: 452-58-4
2,3-Diaminopyridine

: 56995-20-1
Flupirtine

Conditions

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

: 76902-24-4
spiropyridine>

: 56995-20-1
Flupirtine

Conditions

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

: 161263-86-1
5'-<(4-fluorobenzyl)amino>spiropyridine>

: 56995-20-1
Flupirtine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2S2O4 / tetrahydrofuran; H2O / Ambient temperature 2: tetrahydrofuran / Ambient temperature View Scheme

: 16013-85-7
2,6-dicholoro-3-nitropyridine

: 56995-20-1
Flupirtine

Conditions

Conditions	Yield
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

: 27048-04-0
2-amino-6-chloro-3-nitropyridine

: 56995-20-1
Flupirtine

Conditions

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

: 33400-49-6
2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine

: 56995-20-1
Flupirtine

Conditions

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

: 140-75-0
para-fluorobenzylamine

: 56995-20-1
Flupirtine

Conditions

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

: 56995-20-1
Flupirtine

: 110-16-7
maleic acid

: flupirtine maleate

Conditions

Conditions	Yield
In Isopropyl acetate; dimethyl sulfoxide at 55℃; for 1h; Temperature; Solvent; Inert atmosphere;	96%

: 56995-20-1
Flupirtine

: 5-(4-fluorobenzylamino)-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-one

Conditions

Conditions	Yield
at 200℃; for 0.5h;	88%

: 459-57-4
4-fluorobenzaldehyde

: 56995-20-1
Flupirtine

: C37H37F3N8O4

Conditions

Conditions	Yield
With triethylamine In ethanol for 16h; Reflux;	70%

: 15307-86-5
[2-(2,6-dichloroanilino)phenyl]acetic acid

: 56995-20-1
Flupirtine

: C15H17FN4O2*C14H11Cl2NO2

Conditions

Conditions	Yield
In toluene at 60℃; Inert atmosphere;	66%

: 56995-20-1
Flupirtine

: 74-88-4
methyl iodide

: ethyl [2-amino-6-(4-fluorobenzylamino)pyridine-3-yl](methyl)carbamate

Conditions

Conditions	Yield
Stage #1: Flupirtine With sodium hydride In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Darkness; Stage #2: methyl iodide In tetrahydrofuran; hexane Inert atmosphere;	40%

: 56995-20-1
Flupirtine

: 76-05-1
trifluoroacetic acid

: 2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)-pyridine triflutate

Conditions

Conditions	Yield
In isopropyl alcohol at -5 - 30℃;
In isopropyl alcohol at 30℃;

: 56995-20-1
Flupirtine

: 110-16-7
maleic acid

: flupirtine maleate

Conditions

Conditions	Yield
In isopropyl alcohol at 17 - 60℃; Product distribution / selectivity;
In isopropyl alcohol at 20 - 60℃; Product distribution / selectivity;
In isopropyl alcohol at 20 - 60℃; Product distribution / selectivity;
In isopropyl alcohol at 60℃;

: 56995-20-1
Flupirtine

: 64-19-7
acetic acid

: 1198579-27-9
2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)-pyridine acetate

Conditions

Conditions	Yield
In ethanol at -15 - 60℃; Inert atmosphere;
In ethanol at 40 - 60℃; Inert atmosphere;

: 56995-20-1
Flupirtine

: 802294-64-0
propionic acid

: 1198579-28-0
2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)-pyridine propionate

Conditions

Conditions	Yield
In isopropyl alcohol at -5 - 60℃; Inert atmosphere;
In isopropyl alcohol at 50 - 60℃; Inert atmosphere;

: 104-15-4
toluene-4-sulfonic acid

: 56995-20-1
Flupirtine

: 1200119-41-0
2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)-pyridine tosilate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 50℃;
In isopropyl alcohol at 20 - 40℃;

: 75-75-2
methanesulfonic acid

: 56995-20-1
Flupirtine

: 1200119-31-8
2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)-pyridine mesilate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 60℃; for 0.5h; Inert atmosphere;
In isopropyl alcohol at 20 - 60℃; Inert atmosphere;

: 56995-20-1
Flupirtine

: 98-11-3
benzenesulfonic acid

: 1200119-39-6
2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)-pyridine besilate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 60℃; for 0.5h; Inert atmosphere;
In isopropyl alcohol at 20 - 60℃; Inert atmosphere;

: 104-15-4
toluene-4-sulfonic acid

: 56995-20-1
Flupirtine

: 2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)pyridine tosilate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 40℃;

: 56995-20-1
Flupirtine

: 76-05-1
trifluoroacetic acid

: (x)C2HF3O2*C15H17FN4O2

Conditions

Conditions	Yield
In isopropyl alcohol at 30℃; for 0.5h;

: 75-75-2
methanesulfonic acid

: 56995-20-1
Flupirtine

: 2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)pyridine mesylate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 60℃; Inert atmosphere;

: 56995-20-1
Flupirtine

: 64-19-7
acetic acid

: 2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)pyridine acetate

Conditions

Conditions	Yield
In ethanol at 40 - 60℃; Inert atmosphere;

: 56995-20-1
Flupirtine

: 802294-64-0
propionic acid

: 2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)pyridine propionate

Conditions

Conditions	Yield
In isopropyl alcohol at 60℃; Inert atmosphere;

: 56995-20-1
Flupirtine

: 98-11-3
benzenesulfonic acid

: 2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)pyridine besilate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 60℃; Inert atmosphere;

: 56995-20-1
Flupirtine

: ethyl 5-(4-fluorobenzylamino)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h / 200 °C 2: acetonitrile; N,N-dimethyl-formamide / 75 °C View Scheme

: 56995-20-1
Flupirtine

: ethyl 5-[(ethoxycarbonyl)(4-fluorobenzyl)amino]-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h / 200 °C 2: acetonitrile; N,N-dimethyl-formamide / 75 °C View Scheme

Flupirtine Specification

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.

Flupirtine is prepared by reaction of 2-amino-3-nitro-6-chloro pyridine with p-fluorobenzyl amine.

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

Product Name

Flupirtine

Synthetic route

Flupirtine Specification

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