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443913-73-3

Basic Information
CAS No.: 443913-73-3
Name: Vandetanib
Article Data: 7
Molecular Structure:
Molecular Structure of 443913-73-3 (Vandetanib)
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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

443913-73-3

vandetanib

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity; Saturated solution;
367-24-8

4-bromo-2-fluoroaniline

443913-73-3

vandetanib

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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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    Superlist Name: Vandetanib Formula: C22H24BrFN4O2 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]quinazo

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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