CAS No.74191-85-8,[4-(4-Amino-6,7-dimethoxy-quinazolin-2- yl)piperazin-1-yl]-(2,5-dioxabi cyclo[4.4.0]deca-6,8,10-trien-4-yl)methanone Suppliers

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Basic Information

Molecular Structure:
CAS No.:	74191-85-8
Name:	[4-(4-Amino-6,7-dimethoxy-quinazolin-2- yl)piperazin-1-yl]-(2,5-dioxabi cyclo[4.4.0]deca-6,8,10-trien-4-yl)methanone
Article Data:	9

Formula:	C₂₃H₂₅N₅O₅
Molecular Weight:	451.482
Synonyms:	Piperazine,1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]-(9CI);[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](2,3-dihydro-1,4-benzodioxin-2-yl)methanone;Doxazosine;UK 33274;piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]-;2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)pipérazin-1-yl]-6,7-diméthoxyquinazolin-4-amine;
Density:	1.371 g/cm³
Melting Point:	289-290 °C
Boiling Point:	718 °C at 760 mmHg
Flash Point:	388 °C
Hazard Symbols:	T,Xi
Risk Codes:	R23/24/25; R34; R40; R43; R36/37/38; R38
PSA:	175.02000
LogP:	2.88670

Synthetic route

: 23680-84-4
2-chloro-6,7-dimethoxyquinazolin-4-amine

: 70918-00-2
(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
In butan-1-ol Reflux;	88%
In butan-1-ol for 5h; Heating;	83%

: 3663-80-7, 34385-93-8, 70918-53-5, 70918-54-6
1,4-benzodioxane-2-carboxylic acid

: 60547-97-9
4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 5.16667h;	80%

: 4739-94-0
ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / 6 h / 70 - 80 °C 2: 83 percent / butan-1-ol / 5 h / Heating View Scheme

: 120-80-9
benzene-1,2-diol

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / potassium hydroxide; polyethylene glycol-400; potassium carbonate / toluene / 3.75 h / Heating 2: 65 percent / 6 h / 70 - 80 °C 3: 83 percent / butan-1-ol / 5 h / Heating View Scheme

: 1246188-97-5
(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(1H-imidazol-1-yl)methanone

: 60547-97-9
4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
In tetrahydrofuran at 25 - 28℃; Product distribution / selectivity;

: 3663-80-7, 34385-93-8, 70918-53-5, 70918-54-6
1,4-benzodioxane-2-carboxylic acid

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 - 25 °C 2: tetrahydrofuran / 25 - 28 °C View Scheme
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: butan-1-ol / Reflux View Scheme

: 3663-82-9
2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide; potassium permanganate / water / 0 °C 2: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1: potassium hydroxide; potassium permanganate / water / 0 °C 2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 4: butan-1-ol / Reflux View Scheme

: 533-58-4
2-Iodophenol

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 4: potassium hydroxide; potassium permanganate / water / 0 °C 5: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 4: potassium hydroxide; potassium permanganate / water / 0 °C 5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 7: butan-1-ol / Reflux View Scheme

Yield

Multi-step reaction with 5 steps
1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
4: potassium hydroxide; potassium permanganate / water / 0 °C
5: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C
View Scheme

Multi-step reaction with 7 steps
1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
4: potassium hydroxide; potassium permanganate / water / 0 °C
5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
6: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
7: butan-1-ol / Reflux
View Scheme

: C13H15IO5

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 3: potassium hydroxide; potassium permanganate / water / 0 °C 4: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme
Multi-step reaction with 6 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 3: potassium hydroxide; potassium permanganate / water / 0 °C 4: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 6: butan-1-ol / Reflux View Scheme

Yield

Multi-step reaction with 4 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
3: potassium hydroxide; potassium permanganate / water / 0 °C
4: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C
View Scheme

Multi-step reaction with 6 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C
2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
3: potassium hydroxide; potassium permanganate / water / 0 °C
4: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
5: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
6: butan-1-ol / Reflux
View Scheme

: 2-(2-iodophenoxy)propane-1,3-diol

: 74191-85-8
doxazosin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 2: potassium hydroxide; potassium permanganate / water / 0 °C 3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme
Multi-step reaction with 5 steps 1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 2: potassium hydroxide; potassium permanganate / water / 0 °C 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 5: butan-1-ol / Reflux View Scheme

Yield

Multi-step reaction with 3 steps
1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
2: potassium hydroxide; potassium permanganate / water / 0 °C
3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C
View Scheme

Multi-step reaction with 5 steps
1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere
2: potassium hydroxide; potassium permanganate / water / 0 °C
3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere
4: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
5: butan-1-ol / Reflux
View Scheme

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Specification

The Doxazosin, with the CAS registry number 74191-85-8, has the systematic name of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](2,3-dihydro-1,4-benzodioxin-2-yl)methanone. Its classification codes are: Adrenergic Agents; Adrenergic Antagonists; Adrenergic alpha-antagonists; Antihypertensive agents; Cardiovascular Agents; Neurotransmitter Agents. The molecular formula of this chemical is C₂₃H₂₅N₅O₅.

The physical properties of Doxazosin are as following: (1)ACD/LogP: 0.65; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.33; (4)ACD/LogD (pH 7.4): 0.6; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.65; (7)ACD/KOC (pH 5.5): 5.62; (8)ACD/KOC (pH 7.4): 48.37; (9)#H bond acceptors: 10; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 89.49 Å²; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 121.23 cm³; (15)Molar Volume: 329.2 cm³; (16)Polarizability: 48.06×10^-24cm³; (17)Surface Tension: 64.9 dyne/cm; (18)Density: 1.371 g/cm³; (19)Flash Point: 388 °C; (20)Enthalpy of Vaporization: 104.92 kJ/mol; (21)Boiling Point: 718 °C at 760 mmHg; (22)Vapour Pressure: 1.83E-20 mmHg at 25°C.

Preparation of Doxazosin: It can be prepared by 4-Amino-2-chloro-6,7 -dimethoxy-quinazoline and 2-(1-carboxymethyl piperazine carbonyl)-1,4-Benzodioxan.

Doxazosin can be prepared by 4-Amino-2-chloro-6,7 -dimethoxy-quinazoline and 2-(1-carboxymethyl piperazine carbonyl)-1,4-Benzodioxan

Uses of Doxazosin: It is used to treat high blood pressure and urinary retention associated with benign prostatic hyperplasia. It is a kind of alpha-1 adrenergic receptor blocker that inhibits the binding of norepinephrine to the alpha-1 receptors on the membrane of vascular smooth muscle cells. And this primary effect of the inhibition is relaxed vascular smooth muscle tone, which decreases peripheral vascular resistance, leading to decreased blood pressure.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4Oc5c(OC4)cccc5
(2)InChI: InChI=1/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
(3)InChIKey: RUZYUOTYCVRMRZ-UHFFFAOYAW