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388082-78-8

Basic Information
CAS No.: 388082-78-8
Name: Lapatinib ditosylate
Article Data: 31
Molecular Structure:
Molecular Structure of 388082-78-8 (Lapatinib ditosylate)
Formula: C29H26ClFN4O4S.2(C7H8O3S).H2O
Molecular Weight: 925.477
Synonyms: GW572016F;Tykerb;UNII-G873GX646R;Lapatinib ditosylate;
EINECS: 642-915-3
Density: 1.381 g/cm3
Melting Point: 237 - 239 °C
Boiling Point: 750.7 °C at 760 mmHg
Flash Point: 407.8 °C
Appearance: colourless to light-yellow crystal
Hazard Symbols: Xi,N
Risk Codes: R43; R51/53
PSA: 249.46000
LogP: 12.26450
Synthetic route
104458-24-4

2-(methylsulfonyl)ethylamine hydrochloride

104-15-4

toluene-4-sulfonic acid

231278-84-5

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

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Stage #1: 2-(methylsulfonyl)ethylamine hydrochloride; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With tetrabutylammomium bromide; triethylamine In tetrahydrofuran at 30℃; for 3h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 4h;
Stage #3: toluene-4-sulfonic acid In tetrahydrofuran at 50℃; for 1h;
94.9%
Stage #1: 2-(methylsulfonyl)ethylamine hydrochloride; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With acetic acid; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 12h;
Stage #3: toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 12h;
82.8%
Stage #1: 2-(methylsulfonyl)ethylamine hydrochloride; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With acetic acid; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 35℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran; N,N-dimethyl-formamide at 20 - 25℃; for 2h;
Stage #3: toluene-4-sulfonic acid
72%
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 tetrahydrofuran; acetic acid at 30 - 35℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran; acetic acid at 22℃; for 2 - 4h;
Stage #3: toluene-4-sulfonic acid With sodium hydroxide In tetrahydrofuran; acetic acid
49773-20-8

2-Methanesulfonyl-ethylamine

104-15-4

toluene-4-sulfonic acid

231278-84-5

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

388082-78-8

lapatinib ditosylate

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;
Stage #3: toluene-4-sulfonic acid In methanol; dichloromethane
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%

N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine hydrochloride

104-15-4

toluene-4-sulfonic acid

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Stage #1: N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine hydrochloride With sodium hydroxide In water; ethyl acetate pH=~ 10; Inert atmosphere;
Stage #2: toluene-4-sulfonic acid In N,N-dimethyl-formamide at 40℃; for 1h;
90.1%
1383531-68-7

lapatinib monohydrochloride

104-15-4

toluene-4-sulfonic acid

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Stage #1: lapatinib monohydrochloride With sodium hydroxide In water; ethyl acetate pH=10; Inert atmosphere;
Stage #2: toluene-4-sulfonic acid In N,N-dimethyl-formamide at 40℃; for 1h;
90.1%
49773-20-8

2-Methanesulfonyl-ethylamine

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

104-15-4

toluene-4-sulfonic acid

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde tosylate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; isopropyl alcohol for 1h; Industrial scale;
Stage #2: With sodium tris(acetoxy)borohydride; isopropyl alcohol In tetrahydrofuran at 20℃; for 1.66667h; Industrial scale;
Stage #3: toluene-4-sulfonic acid Industrial scale; Further stages;
88%
903597-10-4

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

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Multi-step reaction with 5 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
5: methanol / 3 h / Reflux
View Scheme
27329-70-0

5-formylfurane-2-boronic acid

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Multi-step reaction with 4 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
4: methanol / 3 h / 25 - 65 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine; palladium / tetrahydrofuran; ethanol / 7 h / 65 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.33 h / 20 °C
2.2: 2 h / 40 °C
2.3: 3 h / 25 - 40 °C
3.1: tetrahydrofuran / 6 h / 65 °C
View Scheme
Multi-step reaction with 3 steps
1.1: palladium 10% on activated carbon / isopropyl methanesulfonate / 0.08 h
1.2: 3 h / 70 °C
3.1: tetrahydrofuran / 4 h / 20 - 55 °C
View Scheme
Multi-step reaction with 4 steps
1.1: palladium 10% on activated carbon / isopropyl methanesulfonate / 0.08 h
1.2: 3 h / 70 °C
2.1: isopropyl methanesulfonate; water / 4.08 - 4.17 h / 25 - 65 °C
3.1: acetic acid; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 30 - 35 °C
3.2: 2.25 h / 22 - 23 °C
3.3: 0.5 h
4.1: tetrahydrofuran / 4 h / 20 - 55 °C
View Scheme
202197-26-0

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

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Multi-step reaction with 6 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
6: methanol / 3 h / 25 - 65 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1-methyl-pyrrolidin-2-one / 0.5 h / 20 - 25 °C
1.2: 0.33 - 0.5 h
2.1: palladium 10% on activated carbon / ethanol; water / 0.08 h
2.2: 3 h / 70 °C
3.1: tetrahydrofuran; ethanol; isopropyl methanesulfonate; water / 2.08 h / 20 - 65 °C
4.1: acetic acid; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 30 - 35 °C
4.2: 2 - 4 h / 22 - 23 °C
4.3: 0.5 h
5.1: tetrahydrofuran; water / 3 - 4 h / 20 - 63 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tributyl-amine / toluene / 70 - 80 °C
1.2: 2 h / Heating / reflux
2.1: palladium 10% on activated carbon / ethanol; water / 0.08 h
2.2: 3 h / 70 °C
3.1: tetrahydrofuran; ethanol; isopropyl methanesulfonate; water / 2.08 h / 20 - 65 °C
4.1: acetic acid; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 30 - 35 °C
4.2: 2 - 4 h / 22 - 23 °C
4.3: 0.5 h
5.1: tetrahydrofuran; water / 3 - 4 h / 20 - 63 °C
View Scheme
1227853-05-5

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

388082-78-8

lapatinib ditosylate

Conditions
ConditionsYield
Multi-step reaction with 5 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
5: methanol / 3 h / 25 - 65 °C
View Scheme
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231277-92-2
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    Name: Lapatinib ditosylate monohydrate Synonyms: Lapatinib ditosylate hydrate; N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine bis(4-methylbenzenesulfonate) monohydrate CAS:

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  • 388082-78-8CAS NO.: 388082-78-8

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    388082-78-8CAS NO.: 388082-78-8

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Chemistry

Molecular Formula of Lapatinib ditosylate (CAS NO.388082-78-8): C29H26ClFN4O4S.2(C7H8O3S)
Molecular Weight: 925.46 g/mol
Flash Point: 407.8 °C
Enthalpy of Vaporization: 109.42 kJ/mol
Boiling Point: 750.7 °C at 760 mmHg
Vapour Pressure: 2.03E-22 mmHg at 25 °C
Structure of Lapatinib ditosylate (CAS NO.388082-78-8):
                
IUPAC Name: N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine ; 4-Methylbenzenesulfonic acid ; Hydrate
Product Category of Lapatinib ditosylate (CAS NO.388082-78-8): Anti-neoplastic

Specification

  Lapatinib ditosylate , its cas register number is 388082-78-8. It also can be called N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine bis(4-methylbenzenesulfonate) ; and Tykerb .