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Lapatinib
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Name

Lapatinib

 EINECS 1806241-263-5
CAS No. 231277-92-2 Density 1.381 g/cm3
PSA 114.73000 LogP 7.68380
Solubility N/A Melting Point N/A
Formula C29H26ClFN4O4S Boiling Point 750.7 °C at 760 mmHg
Molecular Weight 581.067 Flash Point 407.8 °C
Transport Information N/A Appearance Powder
Safety Risk Codes R10; R23/24/25; R34; R36/37/38
Molecular Structure Molecular Structure of 231277-92-2 (Lapatinib) Hazard Symbols T,F
Synonyms

GW572016;N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine;Lapatinib base;Lapatinib & its intermediates;Lapatinib(TINIBS);GW 572016;GSK 572016;Lapatinib [INN];

Article Data 37

Lapatinib Synthetic route

104458-24-4

2-(methylsulfonyl)ethylamine hydrochloride

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: 2-(methylsulfonyl)ethylamine hydrochloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.333333h;
Stage #2: 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With acetic acid In tetrahydrofuran at 40℃; for 2h;
Stage #3: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 25 - 40℃; for 3h; Concentration;		100%
Stage #1: 2-(methylsulfonyl)ethylamine hydrochloride; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 50 - 60℃; for 4h;
Stage #2: With sodium cyanoborohydride In isopropyl alcohol at 20℃; for 2h;		92.6%
Stage #1: 2-(methylsulfonyl)ethylamine hydrochloride With sodium sulfate; triethylamine In methanol at 0℃; for 0.333333h;
Stage #2: 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With formic acid; sodium cyanoborohydride In tetrahydrofuran; methanol; N,N-dimethyl-formamide for 2h; pH=5 - 6;		82%

C27H19ClFN3O3

104458-24-4

2-(methylsulfonyl)ethylamine hydrochloride

231277-92-2

lapatanib

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25 - 30℃; Inert atmosphere;97%
388082-78-8

lapatinib ditosylate

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: lapatinib ditosylate In ethyl acetate at 20℃; for 1h;
Stage #2: With sodium carbonate In water; ethyl acetate for 1h;		96.2%
With sodium carbonate In water; acetonitrile at 5 - 40℃; for 3.58333h;91%
With sodium carbonate In water; ethyl acetate at 22 - 70℃; for 3.25h;56%
50-00-0

formaldehyd

6-(furan-2-yl)-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline

104458-24-4

2-(methylsulfonyl)ethylamine hydrochloride

231277-92-2

lapatanib

Conditions
ConditionsYield
In tetrahydrofuran at 35 - 40℃; for 4h;90.3%

C11H18BNO5S

231278-20-9

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

231277-92-2

lapatanib

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium dihydrogenphosphate In N,N-dimethyl-formamide at 80℃; for 5h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;89.8%
49773-20-8

2-Methanesulfonyl-ethylamine

231278-84-5

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde In methanol; dichloromethane at 20℃;
Stage #2: With hydrogen In methanol; dichloromethane Inert atmosphere;		85%
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine
Stage #2: With toluene-4-sulfonic acid		80%
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With triethylamine In tetrahydrofuran; methanol for 3h;
Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 20℃; Cooling with ice;		70%

C18H22N4O3S

202197-26-0

3-chloro-4-(3-fluorobenzyloxy)aniline

231277-92-2

lapatanib

Conditions
ConditionsYield
With acetic acid for 1h; Reflux; Industrial scale;84.2%
1227853-05-5

N(1)-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethylformamidine

2-amino-5-[5-[[[2-(methanesulfonyl)ethyl]amino]methyl]furan-2-yl]benzonitrile

231277-92-2

lapatanib

Conditions
ConditionsYield
With acetic acid for 1h; Reflux; Industrial scale;82.4%

NEU-0000388

231277-92-2

lapatanib

Conditions
ConditionsYield
With 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 20℃; under 2585.81 - 2844.39 Torr;81.67%
845658-68-6

N-((5-bromofuran-2-yl)methyl)-2-(methylsulfonyl)ethanamine

944549-41-1

N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-6-bromo-quinazolin-4-amine

73183-34-3

bis(pinacol)diborane

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: N-((5-bromofuran-2-yl)methyl)-2-(methylsulfonyl)ethanamine; bis(pinacol)diborane With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 75℃; for 5h; Inert atmosphere;
Stage #2: N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-6-bromo-quinazolin-4-amine In dimethyl sulfoxide at 75℃; for 16h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst;		47%

Lapatinib Specification

1. Introduction of Lapatinib
Lapatinib is one kind of off-white crystaline powder. The IUPAC Name of this chemical is N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine. Lapatinib belongs to Molecular Targeted Antineoplastic;anti-neoplastic;Pharmaceutical intermediate. Besides, the Classification Code of it is Antineoplastic; Antineoplastic Agents; Dual EGFR/erbB2 Inhibitors; Enzyme Inhibitors; Protein Kinase Inhibitors; Tyrosine Kinase Inhibitors. In addition, its solubility in water is 0.007 mg/mL and in 0.1N HCl is 0.001 mg/mL at 25°C.

2. Properties of Lapatinib
Physical properties about Lapatinib are:
(1)H bond acceptors: 8; (2)H bond donors: 2; (3)Freely Rotating Bonds: 10; (4)Polar Surface Area: 97.15 Å2; (5)Index of Refraction: 1.644; (6)Molar Refractivity: 152.46 cm3; (7)Molar Volume: 420.6 cm3; (8)Surface Tension: 57.6 dyne/cm; (9)Density: 1.381 g/cm3; (10)Flash Point: 407.8 °C; (11)Enthalpy of Vaporization: 109.42 kJ/mol; (12)Boiling Point: 750.7 °C at 760 mmHg; (13)Vapour Pressure: 2.03E-22 mmHg at 25°C; (14)Protein binding: >99%; (15)Bioavailability: Variable, increased with food; (16)Half life: 24 hours; (17)Excretion: Mostly fecal; (18)Metabolism of Lapatinib: Hepatic, mostly CYP3A-mediated.

3. Structure Descriptors of Lapatinib
(1)InChI: InChI=1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35)
(2)InChIKey: InChIKey=BCFGMOOMADDAQU-UHFFFAOYSA-N
(3)Smiles: c1cc2ncnc(Nc3ccc(c(c3)Cl)OCc3cccc(c3)F)c2cc1c1oc(cc1)CNCCS(=O)(=O)C

4. Toxicity of Lapatinib
Routes: Oral

5. Uses of Lapatinib
Lapatinib (CAS NO.231277-92-2) is used as a treatment for women's breast cancer in patients. These patients have HER2-positive advanced breast cancer, which has progressed after previous treatment with other chemotherapeutic agents, such as taxane-derived drugs, anthracycline, or trastuzumab. It is used in combination therapy for HER2-positive breast cancer. It is used for the treatment of patients with advanced or metastatic breast cancer whose tumors overexpress HER2 (ErbB2). However, the most common side effects are diarrhea, fatigue, nausea and rashes. Lapatinib is regarded as well tolerated, Like many small molecule tyrosine kinase inhibitors.

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