Name: Vandetanib
SKU: 443913-73-3

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Basic Information

Molecular Structure:
CAS No.:	443913-73-3
Name:	Vandetanib
Article Data:	7

Formula:	C₂₂H₂₄BrFN₄O₂
Molecular Weight:	475.361
Synonyms:	4-(4-Bromo-2-fluoroanilino)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline;CH 331;ZD 6474;Zactima;N-(4-bromo-2-fluoro-phenyl)-6-methoxy-7-[(1-methyl-4-piperidyl)methoxy]quinazolin-4-amine;4-quinazolinamine, N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-;N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-4-quinazolinamine;
EINECS:	669-841-4
Density:	1.406 g/cm³
Melting Point:	240-243 °C
Boiling Point:	538.22 °C at 760 mmHg
Flash Point:	279.306 °C
Appearance:	Yellow solid
Safety:	24/25
PSA:	59.51000
LogP:	5.01510

Synthetic route

: 50-00-0
formaldehyd

: 338992-20-4
4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
Stage #1: formaldehyd; 4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester With formic acid In water at 80℃; for 6.5 - 8.5h; Stage #2: With potassium hydroxide In methanol; water at 60℃; for 2h; Product distribution / selectivity;	94%
Stage #1: formaldehyd; 4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester With formic acid In water at 80℃; for 5 - 6.5h; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 40℃; Product distribution / selectivity;	90.6%
Stage #1: formaldehyd; 4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester With formic acid; water at 95℃; for 4h; Stage #2: With sodium hydroxide In water pH=10.5; Product distribution / selectivity;	88%
Stage #1: formaldehyd; 4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester With formic acid In water at 81℃; for 5h; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 40℃; Product distribution / selectivity;	80.3%

: 367-24-8
4-bromo-2-fluoroaniline

: 264208-72-2
4-chloro-6-methoxy-7-[(1'-methylpiperidin-4'-yl)methoxy]-quinazoline

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
In isopropyl alcohol at 80℃; for 0.533333h; Microwave irradiation;	89%

: 50-00-0
formaldehyd

: 338992-12-4
N-Desmethylvandetanib

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
With sodium triacetoxyborohydride; acetic acid In methanol; dichloromethane; water at 20℃; for 2h;	85%
Stage #1: formaldehyd; N-Desmethylvandetanib With formic acid at 95℃; for 4h; Stage #2: With sodium hydroxide In water pH=11;	45%
With sodium cyanoborohydride In tetrahydrofuran; methanol at 18 - 25℃; for 1h; Product distribution / selectivity;

: 64-18-6
formic acid

: 338992-12-4
N-Desmethylvandetanib

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In methanol; dichloromethane at 20℃; for 2h;	84%

: 50-00-0
formaldehyd

: 64-18-6
formic acid

: 338992-20-4
4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
Stage #1: 4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester With hydrogenchloride In methanol; water at 20℃; Stage #2: formaldehyd; formic acid at 20℃;	78%

...Expand

: 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity; Saturated solution;

: 367-24-8
4-bromo-2-fluoroaniline

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogenchloride / isopropyl alcohol / 2 h / Reflux 2: trifluoroacetic acid / 1 h / Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 20 - 90 °C 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 5: sodium triacetoxyborohydride; acetic acid / methanol; dichloromethane; water / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid / 1 h / 130 °C / Irradiation 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane; methanol / 2 h / 20 °C View Scheme

: 162364-72-9
7-benzyloxy-4-chloro-6-methoxyquinazoline

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogenchloride / isopropyl alcohol / 2 h / Reflux 2: trifluoroacetic acid / 1 h / Reflux 3: potassium carbonate / N,N-dimethyl-formamide / 20 - 90 °C 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 5: sodium triacetoxyborohydride; acetic acid / methanol; dichloromethane; water / 2 h / 20 °C View Scheme

: 196603-96-0
4-(4-bromo-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 - 90 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: sodium triacetoxyborohydride; acetic acid / methanol; dichloromethane; water / 2 h / 20 °C View Scheme

: 768350-54-5
7-(benzyloxy)-N-(4-bromo-2-fluorophenyl)-6-methoxyquinazolin-4-amine hydrochloride

: 443913-73-3
vandetanib

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: trifluoroacetic acid / 1 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 20 - 90 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 4: sodium triacetoxyborohydride; acetic acid / methanol; dichloromethane; water / 2 h / 20 °C View Scheme

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Specification

The Zactima, with the CAS registry number 443913-73-3, has the systematic name of N-(4-bromo-2-fluoro-phenyl)-6-methoxy-7-[(1-methyl-4-piperidyl)methoxy]quinazolin-4-amine. It is a kind of yellow solid, and belongs to the following product categories: Aromatics Compounds; Aromatics; Heterocycles; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. The molecular formula of the chemical is C₂₂H₂₄BrFN₄O₂.

It is an antagonist of the vascular endothelial growth factor receptor (VEGFR) and the epidermal growth factor receptor (EGFR). And it is a kind of medication currently undergoing clinical trials as a potential targeted treatment for non-small-cell lung cancer.

The physical properties of Zactima are as followings: (1)ACD/LogP: 4.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.842; (4)ACD/LogD (pH 7.4): 2.501; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 20.505; (7)ACD/KOC (pH 5.5): 2.49; (8)ACD/KOC (pH 7.4): 113.564; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 59.51 Å²; (13)Index of Refraction: 1.629; (14)Molar Refractivity: 120.039 cm³; (15)Molar Volume: 337.968 cm³; (16)olarizability: 47.587×10^-24cm³; (17)Surface Tension: 53.158 dyne/cm; (18)Density: 1.406 g/cm³; (19)Flash Point: 279.306 °C; (20)Enthalpy of Vaporization: 81.533 kJ/mol; (21)Boiling Point: 538.22 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CN1CCC(CC1)COc2cc3c(cc2OC)c(ncn3)Nc4ccc(cc4F)Br
(2)InChI: InChI=1/C22H24BrFN4O2/c1-28-7-5-14(6-8-28)12-30-21-11-19-16(10-20(21)29-2)22(26-13-25-19)27-18-4-3-15(23)9-17(18)24/h3-4,9-11,13-14H,5-8,12H2,1-2H3,(H,25,26,27)
(3)InChIKey: UHTHHESEBZOYNR-UHFFFAOYAR