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Basic Information
CAS No.: 81403-68-1
Name: Alfuzosin hydrochloride
Article Data: 16
Molecular Structure:
Molecular Structure of 81403-68-1 (Alfuzosin hydrochloride)
Formula: C19H27N5O4.HCl
Molecular Weight: 425.915
Synonyms: Xatral;Prestwick_774;Uroxatral;N-[3-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]propyl]oxolane-2-carboxamide hydrochloride;Alfuzocin hydrochloride;Uroxatral (TN);2-Furancarboxamide,N-[3-[(4-amino-6,7- dimethoxy-2-quinazolinyl)methylamino]propyl]- tetrahydro-,monohydrochloride;Alfuzosin hydrochloride (JAN/USAN);Alfuzosin HCl;
EINECS: 620-512-3
Density: 1.272 g/cm3
Melting Point: 225 °C
Boiling Point: 687.7 °C at 760 mmHg
Flash Point: 369.7 °C
Appearance: White to off-white solid
Hazard Symbols: HarmfulXn
Risk Codes: 22
PSA: 111.83000
LogP: 3.12480
Synthetic route
81403-80-7

alfuzosin

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20 - 25℃;88%
With hydrogenchloride In methanol; isopropyl alcohol at 20℃; for 0.5h; pH=3 - 4; Product distribution / selectivity;85%
With hydrogenchloride In isopropyl alcohol at 20℃; for 0.75 - 1h; Product distribution / selectivity;82%

N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
Stage #1: N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate With sodium hydroxide In dichloromethane; water at 20℃; for 0.5h;
Stage #2: With hydrogenchloride In ethanol; dichloromethane
87.5%
81403-67-0

N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide

23680-84-4

2-chloro-6,7-dimethoxyquinazolin-4-amine

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
In i-Amyl alcohol for 12h; Heating;66%
In i-Amyl alcohol for 10h; Solvent; Reflux;66%
In i-Amyl alcohol for 6h; Solvent; Reflux;65.5%
16874-33-2

tetrahydro-2-furancarboxylic acid

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / tetrahydrofuran / 0.25 h / 5 °C
2: tetrahydrofuran / Ambient temperature
3: 68 percent / H2, 10percent ethanolic NH3 / Rh/C / 80 °C / 43440.4 Torr
4: 66 percent / 3-methyl-butan-1-ol / 12 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride
2: triethylamine / 1,2-dichloro-ethane / 3 h / 5 - 10 °C
3: i-Amyl alcohol / 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: thionyl chloride / 3 h / 35 °C
2: triethylamine / 1,2-dichloro-ethane / 3 h / 5 - 35 °C
3: palladium on activated charcoal; ammonium formate / methanol / 2 h / Reflux
4: i-Amyl alcohol / 10 h / Reflux
View Scheme
72104-44-0

tetrahydro-N-(3-cyanopropyl)-N-methylfurancarboxamide

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / H2, 10percent ethanolic NH3 / Rh/C / 80 °C / 43440.4 Torr
2: 66 percent / 3-methyl-butan-1-ol / 12 h / Heating
View Scheme
81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / Ambient temperature
2: 68 percent / H2, 10percent ethanolic NH3 / Rh/C / 80 °C / 43440.4 Torr
3: 66 percent / 3-methyl-butan-1-ol / 12 h / Heating
View Scheme
76362-29-3

N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine

1005197-73-8

1-(tetrahydrofuran-2-ylcarbonyl)-1H-imidazole

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
Stage #1: N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine; 1-(tetrahydrofuran-2-ylcarbonyl)-1H-imidazole In dichloromethane at 38 - 40℃;
Stage #2: With hydrogenchloride In ethanol; isopropyl alcohol
1100050-87-0

(R,S)-N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide acetate

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol Product distribution / selectivity; Heating / reflux;
52449-98-6

tetrahydrofuran-2-carbonyl chloride

76362-29-3

N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
Stage #1: tetrahydrofuran-2-carbonyl chloride; N1-methyl-N1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1,3-propanediamine In toluene at 25 - 30℃;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
Stage #3: With hydrogenchloride In methanol; isopropyl alcohol pH=1 - 2;
52449-98-6

tetrahydrofuran-2-carbonyl chloride

81403-68-1

alfuzosin hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / 1,2-dichloro-ethane / 3 h / 5 - 35 °C
2: palladium on activated charcoal; ammonium formate / methanol / 2 h / Reflux
3: i-Amyl alcohol / 10 h / Reflux
View Scheme
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81403-80-7
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Specification

The IUPAC name of Xatral is N-[3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)-methylamino]propyl]oxolane-2-carboxamide hydrochloride. With the CAS registry number 81403-68-1, it is also named as Alfuzosin hydrochloride [USAN]; 2-Furancarboxamide, N-(3-((4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-, monohydrochloride (+-)-. The product's categories are APIs, antihypertensive, treatment of BPH, intermediates & fine chemicals, pharmaceuticals and alfuzosin. It is white to off-white solid which is harmful if swallowed.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.43; (4)ACD/LogD (pH 7.4): -2.33; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 9; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Enthalpy of Vaporization: 102.62 kJ/mol; (13)Vapour Pressure: 3.75E-19 mmHg at 25°C; (14)Rotatable Bond Count: 8; (15)Tautomer Count: 6; (16)Exact Mass: 425.182982; (17)MonoIsotopic Mass: 425.182982; (18)Topological Polar Surface Area: 112; (19)Heavy Atom Count: 29.

Preparation of Xatral: It can obtained by 2-chloro-6,7-dimethoxy-quinazolin-4-ylamine and tetrahydro-N-[3-(methylamino)propyl]-furancarboxamide. This reaction needs solvent 3-methyl-butan-1-ol by heating. The reaction time is 12 hours. The yield is 66%.

Uses of Xatral: It is a-1- Adrenoceptor antagonist structurally similar to prozosin. It is used to treat the signs and symptoms of benign enlargement of the prostate (benign prostatic hyperplasia or BPH).

People can use the following data to convert to the molecule structure.
1. SMILES: O=C(NCCCN(c2nc1cc(OC)c(OC)cc1c(n2)N)C)C3OCCC3.Cl;
2. InChI: InChI=1/C19H27N5O4.ClH/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19;/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23);1H.

The following is the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 200mg/kg (200mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 2569, 2000.
mouse LD50 intravenous 235mg/kg (235mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 2569, 2000.
rat LD50 intravenous 146mg/kg (146mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 2569, 2000.