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inquiryLapatinib Manufacturer CAS No.231277-92-2 Product Name: Lapatinib Synonyms: N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine; 4-Quinazolinam
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inquiryHubei Vanz Pharm Co., is the leading manufacture of APIs, supplements raw powder and some customization products. located in Wuhan, Hubei province. We are one of the most professional company in pharm/chemical industry for more than 10 years. We e
Name Lapatinib Synonyms N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine Molecular Structu
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inquiryName Lapatinib Synonyms N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]quinazolin-4-amine Molecular Formul
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Cas:231277-92-2
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inquiryName:Lapatinib CAS NO: 231277-92-2 Molecular formula:C29H26ClFN4O4S Molecular weight:581.0575 Product Quality 12 years of chemical raw materials Mature operation of the industry System stability Data storage Security without vulnerability
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inquiry[English Name] Lapatinib [Test Method]HPLC [CAS No.] 231277-92-2 [Mol. Formula]C29H26ClFN4O4S [Purity]> 99% by HPLC [Packaging]1KG,25KG/DRUM... Package and quantity according to customer's detail requirement [Remark] In stock,
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inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
2-(methylsulfonyl)ethylamine hydrochloride
5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde
lapatanib
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 25 - 30℃; Inert atmosphere; | 97% |
lapatinib ditosylate
lapatanib
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 35 - 40℃; for 4h; | 90.3% |
N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine
lapatanib
Conditions | Yield |
---|---|
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% |
2-Methanesulfonyl-ethylamine
5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde
lapatanib
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With acetic acid for 1h; Reflux; Industrial scale; | 84.2% |
N(1)-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethylformamidine
lapatanib
Conditions | Yield |
---|---|
With acetic acid for 1h; Reflux; Industrial scale; | 82.4% |
lapatanib
Conditions | Yield |
---|---|
With 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 20℃; under 2585.81 - 2844.39 Torr; | 81.67% |
N-((5-bromofuran-2-yl)methyl)-2-(methylsulfonyl)ethanamine
N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-6-bromo-quinazolin-4-amine
bis(pinacol)diborane
lapatanib
Conditions | Yield |
---|---|
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% |
3-chloro-4-(3-fluorobenzyloxy)nitrobenzene
lapatanib
Conditions | Yield |
---|---|
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 |
4-chloro-6-iodoquinazoline
lapatanib
Conditions | Yield |
---|---|
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 |
2-chloro-4-nitrophenol
lapatanib
Conditions | Yield |
---|---|
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 |
1-(Bromomethyl)-3-fluorobenzene
lapatanib
Conditions | Yield |
---|---|
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 |
N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine
lapatanib
Conditions | Yield |
---|---|
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 |
3-chloro-4-(3-fluorobenzyloxy)aniline
lapatanib
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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; |
N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl)ethylimino)methyl)furan-2-yl)quinazolin-4-amine
lapatanib
Conditions | Yield |
---|---|
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; |
anthranilic acid nitrile
lapatanib
Conditions | Yield |
---|---|
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 |
5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde
lapatanib
Conditions | Yield |
---|---|
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 |
5-iodoanthranilonitrile
lapatanib
Conditions | Yield |
---|---|
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 |
N’-(2-cyano-4-iodophenyl)-N,N-dimethyl formamidine
lapatanib
Conditions | Yield |
---|---|
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 |
5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde hydrochloride
2-(methylsulfonyl)ethylamine hydrochloride
lapatanib
Conditions | Yield |
---|---|
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 |
N-((5-(4-chloro-quinazoline-6-yl)furan-2-yl)methyl)-2-methylsulfonyl ethylamine
3-chloro-4-(3-fluorobenzyloxy)aniline
lapatanib
Conditions | Yield |
---|---|
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℃; |
5-formylfurane-2-boronic acid
lapatanib
Conditions | Yield |
---|---|
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 |
N(1)-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethylformamidine
lapatanib
Conditions | Yield |
---|---|
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 |
2-Methanesulfonyl-ethylamine
lapatanib
Conditions | Yield |
---|---|
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 |
2-(diethoxymethyl)furan
lapatanib
Conditions | Yield |
---|---|
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 |
5-formylfurane-2-boronic acid
N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine
lapatanib
Conditions | Yield |
---|---|
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 |
lapatanib
lapatinib hydrogen bromide salt
Conditions | Yield |
---|---|
With hydrogen bromide In tetrahydrofuran; water at 21 - 60℃; for 23.5833h; | 99.9% |
With hydrogen bromide In methanol; water Reflux; | 83.4% |
lapatanib
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water Reflux; | 96.5% |
With hydrogenchloride In methanol; water at 20℃; | 93% |
With hydrogenchloride In methanol at 25℃; for 20h; |
lapatanib
lapatinib monohydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water at 20℃; | 96% |
With hydrogenchloride In methanol; water Reflux; | 95.2% |
lapatanib
Conditions | Yield |
---|---|
With nitric acid In water; acetonitrile Reflux; | 95.8% |
lapatanib
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In methanol at 20℃; | 95% |
In methanol at 25℃; for 20h; |
lapatanib
benzenesulfonic acid
Conditions | Yield |
---|---|
In acetonitrile at 20℃; Heating; | 94.5% |
Conditions | Yield |
---|---|
In acetonitrile Heating; | 94.3% |
Conditions | Yield |
---|---|
In propan-1-ol at 20℃; Product distribution / selectivity; Heating; | 93.2% |
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 60℃; for 0.5h; | 93% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20 - 57.5℃; | 92.5% |
In methanol at 45 - 65℃; Reflux; | 88% |
In methanol at 25 - 65℃; for 3h; | 88% |
lapatanib
(1S)-10-camphorsulfonic acid
Conditions | Yield |
---|---|
In acetone at 20℃; for 24h; | 89.8% |
Conditions | Yield |
---|---|
In methanol at 21 - 60℃; for 26.5h; | 89.3% |
Conditions | Yield |
---|---|
In ethanol; water Product distribution / selectivity; Heating; | 89% |
lapatanib
naphthalene-1,5-disulfonate
Conditions | Yield |
---|---|
In methanol Reflux; | 86.5% |
Conditions | Yield |
---|---|
In methanol for 1h; Concentration; Solvent; Temperature; Reflux; | 86.2% |
In tetrahydrofuran at 21 - 60℃; for 4h; Product distribution / selectivity; | 62.6% |
Conditions | Yield |
---|---|
In water; acetone at 50 - 55℃; Product distribution / selectivity; | 85.8% |
Conditions | Yield |
---|---|
In acetonitrile Concentration; Solvent; Reflux; | 85.4% |
Conditions | Yield |
---|---|
In isopropyl methanesulfonate; water Product distribution / selectivity; Heating; | 85.1% |
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide In diethyl ether at -20℃; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
In water; acetone at 21℃; for 18.5h; Reflux; | 84.7% |
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; Heating; | 84.6% |
Conditions | Yield |
---|---|
In ethanol Reflux; | 83.4% |
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