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231277-92-2

Basic Information
CAS No.: 231277-92-2
Name: Lapatinib
Molecular Structure:
Molecular Structure of 231277-92-2 (Lapatinib)
Formula: C29H26ClFN4O4S
Molecular Weight: 581.06
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];
EINECS: 1806241-263-5
Density: 1.381 g/cm3
Melting Point:
Boiling Point: 750.7 °C at 760 mmHg
Flash Point: 407.8 °C
Solubility:
Appearance: Powder
Hazard Symbols: T,F
Risk Codes: R10; R23/24/25; R34; R36/37/38
Safety:
Transport Information:
PSA: 114.73000
LogP: 7.68380
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%
443882-99-3

3-chloro-4-(3-fluorobenzyloxy)nitrobenzene

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2 / Pt/C / ethanol; tetrahydrofuran
2: propan-2-ol / 70 °C
3: Pd(OAc)2; PPh3; Et3N / dimethylformamide
4: Na(OAc)3BH; HOAc / CH2Cl2
View Scheme
Multi-step reaction with 5 steps
1.1: platinum on carbon; hydrogen / ethanol / 0.83 h / 1292.9 Torr / High pressure
2.1: isopropyl alcohol / 3.5 h / 70 °C
3.1: bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / Inert atmosphere; Reflux
4.1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 20 °C
5.1: triethylamine / tetrahydrofuran; methanol / 3 h
5.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: iron; hydrogenchloride / ethanol; water / 3 h / 70 °C
2.1: acetic acid / 1.5 h / 90 °C
3.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 5 h / 75 °C / Inert atmosphere
3.2: 16 h / 75 °C
View Scheme
Multi-step reaction with 4 steps
1: zinc; ammonium chloride / ethanol; water / 12 h / 60 °C
2: isopropyl alcohol / Reflux
3: potassium carbonate; palladium diacetate / ethanol; tetrahydrofuran / 2 h / Reflux
4: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 20 °C / 2585.81 - 2844.39 Torr
View Scheme
98556-31-1

4-chloro-6-iodoquinazoline

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: propan-2-ol / 70 °C
2: Pd(OAc)2; PPh3; Et3N / dimethylformamide
3: Na(OAc)3BH; HOAc / CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1: isopropyl alcohol / Reflux
2: potassium carbonate; palladium diacetate / ethanol; tetrahydrofuran / 2 h / Reflux
3: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 20 °C / 2585.81 - 2844.39 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 1 h / 90 °C
1.2: 5 h / 20 - 72 °C
2.1: N-ethyl-N,N-diisopropylamine / palladium 10% on activated carbon / ethanol / 3 h / 70 °C
3.1: tetrahydrofuran; ethanol; water / 4 h / 25 - 65 °C
4.1: acetic acid; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 30 - 35 °C
4.2: 2.25 h / 22 °C
View Scheme
619-08-9

2-chloro-4-nitrophenol

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: K2CO3 / acetonitrile
2: H2 / Pt/C / ethanol; tetrahydrofuran
3: propan-2-ol / 70 °C
4: Pd(OAc)2; PPh3; Et3N / dimethylformamide
5: Na(OAc)3BH; HOAc / CH2Cl2
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate / acetonitrile / 2 h / 20 - 60 °C / Inert atmosphere
2.1: platinum on carbon; hydrogen / ethanol / 0.83 h / 1292.9 Torr / High pressure
3.1: isopropyl alcohol / 3.5 h / 70 °C
4.1: bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / Inert atmosphere; Reflux
5.1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 20 °C
6.1: triethylamine / tetrahydrofuran; methanol / 3 h
6.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / 0.5 h / 20 °C
1.2: Reflux
2.1: iron; hydrogenchloride / ethanol; water / 3 h / 70 °C
3.1: acetic acid / 1.5 h / 90 °C
4.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 5 h / 75 °C / Inert atmosphere
4.2: 16 h / 75 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / acetonitrile / 2 h / 60 °C / Inert atmosphere
2: zinc; ammonium chloride / ethanol; water / 12 h / 60 °C
3: isopropyl alcohol / Reflux
4: potassium carbonate; palladium diacetate / ethanol; tetrahydrofuran / 2 h / Reflux
5: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 20 °C / 2585.81 - 2844.39 Torr
View Scheme
456-41-7

1-(Bromomethyl)-3-fluorobenzene

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: K2CO3 / acetonitrile
2: H2 / Pt/C / ethanol; tetrahydrofuran
3: propan-2-ol / 70 °C
4: Pd(OAc)2; PPh3; Et3N / dimethylformamide
5: Na(OAc)3BH; HOAc / CH2Cl2
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate / acetonitrile / 2 h / 20 - 60 °C / Inert atmosphere
2.1: platinum on carbon; hydrogen / ethanol / 0.83 h / 1292.9 Torr / High pressure
3.1: isopropyl alcohol / 3.5 h / 70 °C
4.1: bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / Inert atmosphere; Reflux
5.1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 20 °C
6.1: triethylamine / tetrahydrofuran; methanol / 3 h
6.2: 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / 0.5 h / 20 °C
1.2: Reflux
2.1: iron; hydrogenchloride / ethanol; water / 3 h / 70 °C
3.1: acetic acid / 1.5 h / 90 °C
4.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 5 h / 75 °C / Inert atmosphere
4.2: 16 h / 75 °C
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / acetonitrile / 2 h / 60 °C / Inert atmosphere
2: zinc; ammonium chloride / ethanol; water / 12 h / 60 °C
3: isopropyl alcohol / Reflux
4: potassium carbonate; palladium diacetate / ethanol; tetrahydrofuran / 2 h / Reflux
5: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 20 °C / 2585.81 - 2844.39 Torr
View Scheme
231278-20-9

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

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pd(OAc)2; PPh3; Et3N / dimethylformamide
2: Na(OAc)3BH; HOAc / CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1: triethylamine; 1,2-dimethoxyethane / palladium 10% on activated carbon / methanol / Inert atmosphere
2: triethylamine / methanol / 12 h / Reflux
3: methanol / tetrahydrofuran / 0 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / palladium 10% on activated carbon / 1,2-dimethoxyethane; methanol / 15 h / 45 - 50 °C / Inert atmosphere
2: triethylamine / methanol / 12 h / Reflux
3: sodium tetrahydroborate / tetrahydrofuran; methanol / 4 h / 10 - 15 °C
View Scheme
202197-26-0

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

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: propan-2-ol / 70 °C
2: Pd(OAc)2; PPh3; Et3N / dimethylformamide
3: Na(OAc)3BH; HOAc / CH2Cl2
View Scheme
Multi-step reaction with 5 steps
1: acetic acid / toluene / 2 h / Reflux
2: acetic acid / xylene / 10 h / Reflux
3: triethylamine / palladium 10% on activated carbon / 1,2-dimethoxyethane; methanol / 15 h / 45 - 50 °C / Inert atmosphere
4: triethylamine / methanol / 12 h / Reflux
5: sodium tetrahydroborate / tetrahydrofuran; methanol / 4 h / 10 - 15 °C
View Scheme
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 3.5 h / 70 °C
2.1: bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / Inert atmosphere; Reflux
3.1: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 20 °C
4.1: triethylamine / tetrahydrofuran; methanol / 3 h
4.2: 20 °C / Cooling with ice
View Scheme

5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde 4-methylbenzenesulfonate

104458-24-4

2-(methylsulfonyl)ethylamine hydrochloride

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde 4-methylbenzenesulfonate; 2-(methylsulfonyl)ethylamine hydrochloride With acetic acid; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 30 - 35℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 22 - 23℃; for 2.25h;
Stage #3: With sodium hydroxide In tetrahydrofuran; water for 0.5h;
Stage #1: 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde 4-methylbenzenesulfonate; 2-(methylsulfonyl)ethylamine hydrochloride With sodium acetate; acetic acid In ethyl acetate at 25 - 30℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride In ethyl acetate at 25 - 30℃; for 1.5h;
Stage #3: With water; sodium carbonate In ethyl acetate Product distribution / selectivity;
Stage #1: 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde 4-methylbenzenesulfonate; 2-(methylsulfonyl)ethylamine hydrochloride With acetic acid; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 30 - 35℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 22℃; for 2.25h;
1227853-06-6

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl)ethylimino)methyl)furan-2-yl)quinazolin-4-amine

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl)ethylimino)methyl)furan-2-yl)quinazolin-4-amine With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 15℃;
Stage #2: With water In tetrahydrofuran
With methanol In tetrahydrofuran at 0 - 15℃;
With sodium tetrahydroborate In tetrahydrofuran; methanol at 10 - 15℃; for 4h;
1885-29-6

anthranilic acid nitrile

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Iodine monochloride; acetic acid / 3 h / 25 - 35 °C
2: 2 h / 70 - 75 °C
3: acetic acid / 2 h / 115 - 120 °C
4: triethylamine; 1,2-dimethoxyethane / palladium 10% on activated carbon / methanol / Inert atmosphere
5: triethylamine / methanol / 12 h / Reflux
6: methanol / tetrahydrofuran / 0 - 15 °C
View Scheme
Multi-step reaction with 5 steps
1: acetic acid / 3 h / 25 - 35 °C
2: acetic acid / xylene / 10 h / Reflux
3: triethylamine / palladium 10% on activated carbon / 1,2-dimethoxyethane; methanol / 15 h / 45 - 50 °C / Inert atmosphere
4: triethylamine / methanol / 12 h / Reflux
5: sodium tetrahydroborate / tetrahydrofuran; methanol / 4 h / 10 - 15 °C
View Scheme
Multi-step reaction with 4 steps
1.1: acetic acid; Iodine monochloride / 3 h / 20 °C
2.1: triethylamine; palladium 10% on activated carbon / methanol; 1,2-dimethoxyethane / 3 h / 20 - 45 °C
2.2: 60 °C
3.1: triethylamine; acetic acid / tetrahydrofuran / 1 h / 20 - 35 °C
3.2: 2.5 h / 22 - 25 °C
4.1: acetic acid / 1 h / Reflux; Industrial scale
View Scheme
231278-84-5

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

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / methanol / 12 h / Reflux
2: methanol / tetrahydrofuran / 0 - 15 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / methanol / 12 h / Reflux
2: sodium tetrahydroborate / tetrahydrofuran; methanol / 4 h / 10 - 15 °C
View Scheme
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; ethanol; water / 4 h / 25 - 65 °C
2.1: acetic acid; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 30 - 35 °C
2.2: 2.25 h / 22 °C
View Scheme
132131-24-9

5-iodoanthranilonitrile

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 2 h / 70 - 75 °C
2: acetic acid / 2 h / 115 - 120 °C
3: triethylamine; 1,2-dimethoxyethane / palladium 10% on activated carbon / methanol / Inert atmosphere
4: triethylamine / methanol / 12 h / Reflux
5: methanol / tetrahydrofuran / 0 - 15 °C
View Scheme
Multi-step reaction with 4 steps
1: acetic acid / xylene / 10 h / Reflux
2: triethylamine / palladium 10% on activated carbon / 1,2-dimethoxyethane; methanol / 15 h / 45 - 50 °C / Inert atmosphere
3: triethylamine / methanol / 12 h / Reflux
4: sodium tetrahydroborate / tetrahydrofuran; methanol / 4 h / 10 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine; palladium 10% on activated carbon / methanol; 1,2-dimethoxyethane / 3 h / 20 - 45 °C
1.2: 60 °C
2.1: triethylamine; acetic acid / tetrahydrofuran / 1 h / 20 - 35 °C
2.2: 2.5 h / 22 - 25 °C
3.1: acetic acid / 1 h / Reflux; Industrial scale
View Scheme
903597-10-4

N’-(2-cyano-4-iodophenyl)-N,N-dimethyl formamidine

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid / 2 h / 115 - 120 °C
2: triethylamine; 1,2-dimethoxyethane / palladium 10% on activated carbon / methanol / Inert atmosphere
3: triethylamine / methanol / 12 h / Reflux
4: methanol / tetrahydrofuran / 0 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / 0.25 h / 125 - 130 °C
2.1: palladium 10% on activated carbon; triethylamine / methanol; 1,2-dimethoxyethane / 0.5 h / 50 °C
3.1: triethylamine; sodium sulfate / methanol / 0.33 h / 0 °C
3.2: 2 h / pH 5 - 6
View Scheme
388082-76-6

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

104458-24-4

2-(methylsulfonyl)ethylamine hydrochloride

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: 2-(methylsulfonyl)ethylamine hydrochloride With acetic acid; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde hydrochloride With water In tetrahydrofuran at 20℃; for 4h;
Stage #3: With sodium tris(acetoxy)borohydride In tetrahydrofuran
1334953-75-1

N-((5-(4-chloro-quinazoline-6-yl)furan-2-yl)methyl)-2-methylsulfonyl ethylamine

202197-26-0

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

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: N-((5-(4-chloro-quinazoline-6-yl)furan-2-yl)methyl)-2-methylsulfonyl ethylamine; 3-chloro-4-(3-fluorobenzyloxy)aniline In toluene; butanone at 20 - 90℃;
Stage #2: With sodium hydroxide In tetrahydrofuran; water; toluene; butanone at 20℃;
27329-70-0

5-formylfurane-2-boronic acid

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / palladium 10% on activated carbon / 1,2-dimethoxyethane; methanol / 15 h / 45 - 50 °C / Inert atmosphere
2: triethylamine / methanol / 12 h / Reflux
3: sodium tetrahydroborate / tetrahydrofuran; methanol / 4 h / 10 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / 20 °C
2.1: palladium 10% on activated carbon / methanol / 8 h / Reflux
3.1: N-ethyl-N,N-diisopropylamine; acetic acid / tetrahydrofuran / 1 h / 40 °C
3.2: 3 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / 20 °C
2.1: palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine / methanol / 8 h / Reflux
3.1: N-ethyl-N,N-diisopropylamine; acetic acid / tetrahydrofuran / 1 h / 40 °C
3.2: 3 h / 20 °C
View Scheme
1227853-05-5

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

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid / xylene / 10 h / Reflux
2: triethylamine / palladium 10% on activated carbon / 1,2-dimethoxyethane; methanol / 15 h / 45 - 50 °C / Inert atmosphere
3: triethylamine / methanol / 12 h / Reflux
4: sodium tetrahydroborate / tetrahydrofuran; methanol / 4 h / 10 - 15 °C
View Scheme
49773-20-8

2-Methanesulfonyl-ethylamine

5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde tosylate

231277-92-2

lapatanib

Conditions
ConditionsYield
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde tosylate With acetic acid; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 30 - 35℃; for 2h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20 - 25℃; for 3h;
Stage #3: With water; sodium hydroxide In tetrahydrofuran
13529-27-6

2-(diethoxymethyl)furan

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / 1,2-dimethoxyethane / 2.75 h / -40 - -35 °C / Inert atmosphere
1.2: 2.5 h / -40 - -35 °C
2.1: N-ethyl-N,N-diisopropylamine; acetic acid / tetrahydrofuran / 2 h / 30 - 35 °C
2.2: 3 h / 20 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / hexane; 1,2-dimethoxyethane / 5 h / -50 °C / Inert atmosphere
1.2: 6.5 h / -40 - 20 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine / methanol / 8 h / Reflux
3.1: N-ethyl-N,N-diisopropylamine; acetic acid / tetrahydrofuran / 1 h / 40 °C
3.2: 3 h / 20 °C
View Scheme
27329-70-0

5-formylfurane-2-boronic acid

231278-20-9

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

231277-92-2

lapatanib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: palladium 10% on activated carbon; triethylamine / 1,2-dimethoxyethane; methanol / 14 h / 50 °C
2.1: N-ethyl-N,N-diisopropylamine; acetic acid / tetrahydrofuran / 1 h / 40 °C
2.2: 3 h / 20 °C
View Scheme
231277-92-2

lapatanib

1092929-27-5

lapatinib hydrogen bromide salt

Conditions
ConditionsYield
With hydrogen bromide In tetrahydrofuran; water at 21 - 60℃; for 23.5833h;99.9%
With hydrogen bromide In methanol; water Reflux;83.4%
231277-92-2

lapatanib

lapatinib dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water Reflux;96.5%
With hydrogenchloride In methanol; water at 20℃;93%
With hydrogenchloride In methanol at 25℃; for 20h;
231277-92-2

lapatanib

1383531-68-7

lapatinib monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃;96%
With hydrogenchloride In methanol; water Reflux;95.2%
231277-92-2

lapatanib

lapatinib nitric acid salt

Conditions
ConditionsYield
With nitric acid In water; acetonitrile Reflux;95.8%
231277-92-2

lapatanib

104-15-4

toluene-4-sulfonic acid

({5-[4-({3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}amino)quinazolin-6-yl]furan-2-yl}methyl) [2-(methylsulfonyl)ethyl]azanium 4-methylbenzenesulfonate

Conditions
ConditionsYield
In methanol at 20℃;95%
In methanol at 25℃; for 20h;
231277-92-2

lapatanib

98-11-3

benzenesulfonic acid

N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine ditosylate

Conditions
ConditionsYield
In acetonitrile at 20℃; Heating;94.5%
231277-92-2

lapatanib

110-17-8

(2E)-but-2-enedioic acid

lapatinib difumarate

Conditions
ConditionsYield
In acetonitrile Heating;94.3%
231277-92-2

lapatanib

75-75-2

methanesulfonic acid

lapatinib dimesylate

Conditions
ConditionsYield
In propan-1-ol at 20℃; Product distribution / selectivity; Heating;93.2%
231277-92-2

lapatanib

65-85-0

benzoic acid

lapatinib dibenzoate

Conditions
ConditionsYield
In tetrahydrofuran; water at 60℃; for 0.5h;93%
231277-92-2

lapatanib

104-15-4

toluene-4-sulfonic acid

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
In tetrahydrofuran at 20 - 57.5℃;92.5%
In methanol at 45 - 65℃; Reflux;88%
In methanol at 25 - 65℃; for 3h;88%
231277-92-2

lapatanib

3144-16-9

(1S)-10-camphorsulfonic acid

lapatinib (1S)(+)-camphorsulfonic acid salt

Conditions
ConditionsYield
In acetone at 20℃; for 24h;89.8%
231277-92-2

lapatanib

594-45-6

ethanesulfonic acid

lapatinib diesylate

Conditions
ConditionsYield
In methanol at 21 - 60℃; for 26.5h;89.3%
231277-92-2

lapatanib

110-16-7

maleic acid

lapatinib dimaleate

Conditions
ConditionsYield
In ethanol; water Product distribution / selectivity; Heating;89%
231277-92-2

lapatanib

81-04-9

naphthalene-1,5-disulfonate

lapatinib naphthalene-1,5-disulfonic acid salt

Conditions
ConditionsYield
In methanol Reflux;86.5%
231277-92-2

lapatanib

77-92-9

citric acid

1092929-12-8

lapatinib citric acid salt

Conditions
ConditionsYield
In methanol for 1h; Concentration; Solvent; Temperature; Reflux;86.2%
In tetrahydrofuran at 21 - 60℃; for 4h; Product distribution / selectivity;62.6%
231277-92-2

lapatanib

75-75-2

methanesulfonic acid

1092928-98-7

lapatinib monomesylate

Conditions
ConditionsYield
In water; acetone at 50 - 55℃; Product distribution / selectivity;85.8%
231277-92-2

lapatanib

120-18-3

naphthalene-2-sulfonate

lapatinib naphthalene-2-sulfonic acid salt

Conditions
ConditionsYield
In acetonitrile Concentration; Solvent; Reflux;85.4%
231277-92-2

lapatanib

97-67-6

(S)-Malic acid

1092929-16-2

lapatinib mono-L-malate

Conditions
ConditionsYield
In isopropyl methanesulfonate; water Product distribution / selectivity; Heating;85.1%
231277-92-2

lapatanib

50-78-2

aspirin

alapatinib

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In diethyl ether at -20℃; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;85%
231277-92-2

lapatanib

594-45-6

ethanesulfonic acid

1092929-02-6

lapatinib monoesylate

Conditions
ConditionsYield
In water; acetone at 21℃; for 18.5h; Reflux;84.7%
231277-92-2

lapatanib

97-67-6

(S)-Malic acid

lapatinib di-L-malate

Conditions
ConditionsYield
In ethyl acetate at 20℃; Heating;84.6%
231277-92-2

lapatanib

141-82-2

malonic acid

lapatinib dimalonate

Conditions
ConditionsYield
In ethanol Reflux;83.4%
Downstream Products
388082-78-8
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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.