Erlotinib supplier | CasNO.183321-74-6

Name
Erlotinib
EINECS 689-196-2
CAS No. 183321-74-6
Article Data44
CAS DataBase
Density 1.247 g/cm³
Solubility
Melting Point 223 - 228oC
Formula C₂₂H₂₃N₃O₄
Boiling Point 553.6 °C at 760 mmHg
Molecular Weight 393.442
Flash Point 288.6 °C
Transport Information
Appearance white to off-white powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Erlotinib base;N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;4-Quinazolinamine, N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-,;Taizhou hikong chemical sell Erlotinib;Erlotinib & its intermediates;N-(3-Ethynylphenyl)[6,7-bis(2-methoxyethoxy)quinazolin-4-yl]amine;
PSA 74.73000
LogP 3.47810

Synthetic route

: 54060-30-9
3-acetylenephenylamine

: 183322-18-1
4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
In isopropyl alcohol Concentration; Reflux;	96.6%
In isopropyl alcohol Temperature; Reflux;	96.6%
In isopropyl alcohol at 20℃; Concentration; Temperature; Reflux;	96.6%

: 183319-69-9
erlotinib hydrochloride

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
With sodium hydroxide In water pH=5 - 12; Product distribution / selectivity;	96.3%
With ammonia In water for 2h; pH=9.4; Product distribution / selectivity;	94.3%
With sodium hydroxide In water; ethyl acetate at 20℃; Product distribution / selectivity;

: 950596-59-5
N′-[2-cyano-4,5-{bis(2-methoxyethoxy)phenyl}]-N,N-dimethylformamidine

: 54060-30-9
3-acetylenephenylamine

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide at 125℃; for 1h;	91.5%
With acetic acid In toluene at 125 - 130℃;	66%
With acetic acid at 125 - 130℃; for 3h;	66%
Stage #1: N′-[2-cyano-4,5-{bis(2-methoxyethoxy)phenyl}]-N,N-dimethylformamidine; 3-acetylenephenylamine With acetic acid at 125℃; for 3h; Stage #2: With sodium hydrogencarbonate In water at 0℃;

: 950596-58-4
2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile

: (E)-N,N'-bis(3-ethynylphenyl)methyl ether

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 5h; Temperature; Solvent;	88.2%

: 179688-29-0
6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

: 54060-30-9
3-acetylenephenylamine

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
With titanium tetrachloride; methoxybenzene In 1,4-dioxane for 4h; Inert atmosphere; Reflux;	82%
Stage #1: 6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one With triethylamine; trichlorophosphate In toluene at 20 - 65℃; Inert atmosphere; Stage #2: 3-acetylenephenylamine In isopropyl alcohol; toluene for 2.5h; Inert atmosphere;	64%

: 1312937-41-9
6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline

: 54060-30-9
3-acetylenephenylamine

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Stage #1: 3-acetylenephenylamine In tetrahydrofuran; toluene at 0℃; for 0.5h; Inert atmosphere; Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; toluene at 20℃; for 4h; Product distribution / selectivity;	70%
Stage #1: 3-acetylenephenylamine With n-butyllithium In tetrahydrofuran; toluene at 0℃; Inert atmosphere; Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; toluene at 0 - 20℃; for 4.16667h; Product distribution / selectivity;	70%

: 80407-68-7
3,4-bis(2-methoxyethoxy) benzonitrile

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid / acetic acid / 4 h / 0 °C 2.1: sodium dithionite / water / 3 h / 50 °C 2.2: 0.5 h / 65 °C 3.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 4.1: acetic acid / toluene / 5 h / 60 °C 5.1: toluene / 5 h / 125 °C View Scheme
Multi-step reaction with 4 steps 1.1: nitric acid / acetic acid / 4 h / 0 °C 2.1: sodium dithionite / water / 3 h / 50 °C 2.2: 0.5 h / 65 °C 3.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 4.1: acetic acid / toluene / 125 - 130 °C View Scheme
Multi-step reaction with 4 steps 1.1: acetic acid / 20 °C 1.2: 5 - 55 °C 2.1: palladium on activated charcoal; hydrogen / ethanol / 2.5 h / 20 °C / 2585.81 Torr 3.1: 3 h / 20 °C / Reflux 4.1: acetic acid / 2 h / Reflux View Scheme

: 236750-65-5
2-nitro-4,5-bis(2-methoxyethoxy)benzonitrile

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium dithionite / water / 3 h / 50 °C 1.2: 0.5 h / 65 °C 2.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 3.1: acetic acid / toluene / 5 h / 60 °C 4.1: toluene / 5 h / 125 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium dithionite / water / 3 h / 50 °C 1.2: 0.5 h / 65 °C 2.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 3.1: acetic acid / toluene / 125 - 130 °C View Scheme
Multi-step reaction with 3 steps 1: sodium dithionite / water / 2.5 h / 50 °C 2: acetic acid / toluene / 3 h / 105 °C / Dean-Stark 3: acetic acid / 3 h / 125 - 130 °C View Scheme
Multi-step reaction with 4 steps 1: hydrazine hydrate / water / 3 h / 20 - 30 °C 2: trifluoroacetic acid / ethyl acetate / 4 h / Reflux 3: trichlorophosphate; N,N-dimethyl-formamide / ethyl acetate / 2 h / 70 °C / Inert atmosphere 4: ethanol / 3 h / 40 - 70 °C View Scheme
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / ethanol / 2.5 h / 20 °C / 2585.81 Torr 2: 3 h / 20 °C / Reflux 3: acetic acid / 2 h / Reflux View Scheme

: C24H30N4O4

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
In toluene at 125℃; for 5h;	47 g

: methoxyethoxy 3,4-bis(2-methoxyethoxy)-benzoate

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: water; potassium hydroxide / methanol / 4 h / 20 °C 2.1: urea / 0.5 h / 220 °C 3.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 4.1: nitric acid / acetic acid / 4 h / 0 °C 5.1: sodium dithionite / water / 3 h / 50 °C 5.2: 0.5 h / 65 °C 6.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 7.1: acetic acid / toluene / 5 h / 60 °C 8.1: toluene / 5 h / 125 °C View Scheme
Multi-step reaction with 7 steps 1.1: water; potassium hydroxide / methanol / 4 h / 20 °C 2.1: urea / 0.5 h / 220 °C 3.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 4.1: nitric acid / acetic acid / 4 h / 0 °C 5.1: sodium dithionite / water / 3 h / 50 °C 5.2: 0.5 h / 65 °C 6.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 7.1: acetic acid / toluene / 125 - 130 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: water; potassium hydroxide / methanol / 4 h / 20 °C
2.1: urea / 0.5 h / 220 °C
3.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux
4.1: nitric acid / acetic acid / 4 h / 0 °C
5.1: sodium dithionite / water / 3 h / 50 °C
5.2: 0.5 h / 65 °C
6.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C
7.1: acetic acid / toluene / 5 h / 60 °C
8.1: toluene / 5 h / 125 °C
View Scheme

Multi-step reaction with 7 steps
1.1: water; potassium hydroxide / methanol / 4 h / 20 °C
2.1: urea / 0.5 h / 220 °C
3.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux
4.1: nitric acid / acetic acid / 4 h / 0 °C
5.1: sodium dithionite / water / 3 h / 50 °C
5.2: 0.5 h / 65 °C
6.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C
7.1: acetic acid / toluene / 125 - 130 °C
View Scheme

: 1418289-91-4
3,4-bis(2-methoxyethoxy)-benzamide

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 2.1: nitric acid / acetic acid / 4 h / 0 °C 3.1: sodium dithionite / water / 3 h / 50 °C 3.2: 0.5 h / 65 °C 4.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 5.1: acetic acid / toluene / 5 h / 60 °C 6.1: toluene / 5 h / 125 °C View Scheme
Multi-step reaction with 5 steps 1.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 2.1: nitric acid / acetic acid / 4 h / 0 °C 3.1: sodium dithionite / water / 3 h / 50 °C 3.2: 0.5 h / 65 °C 4.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 5.1: acetic acid / toluene / 125 - 130 °C View Scheme

: 819813-71-3
3,4-bis(2-methoxyethoxy)-benzoic acid

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: urea / 0.5 h / 220 °C 2.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 3.1: nitric acid / acetic acid / 4 h / 0 °C 4.1: sodium dithionite / water / 3 h / 50 °C 4.2: 0.5 h / 65 °C 5.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 6.1: acetic acid / toluene / 5 h / 60 °C 7.1: toluene / 5 h / 125 °C View Scheme
Multi-step reaction with 6 steps 1.1: urea / 0.5 h / 220 °C 2.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 3.1: nitric acid / acetic acid / 4 h / 0 °C 4.1: sodium dithionite / water / 3 h / 50 °C 4.2: 0.5 h / 65 °C 5.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 6.1: acetic acid / toluene / 125 - 130 °C View Scheme
Multi-step reaction with 10 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C 2: triethylamine / dichloromethane / 0 - 20 °C 3: triethylamine; dmap / dichloromethane / 24 h / 20 °C 4: sodium hydroxide / methanol / 2 h / 20 °C 5: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere 6: sodium hydroxide / ethanol / 20 °C 7: ethanol / 1 h / Reflux 8: hydrogenchloride / water / 2 h / 100 - 105 °C 9: trichlorophosphate / toluene / 4 h / Reflux 10: pyridine / isopropyl alcohol / 4 h / Reflux View Scheme

: 950596-58-4
2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 2: acetic acid / toluene / 5 h / 60 °C 3: toluene / 5 h / 125 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid / toluene / 3 h / 105 °C / Dean-Stark 2: acetic acid / 3 h / 125 - 130 °C View Scheme

: 950596-59-5
N′-[2-cyano-4,5-{bis(2-methoxyethoxy)phenyl}]-N,N-dimethylformamidine

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / toluene / 5 h / 60 °C 2: toluene / 5 h / 125 °C View Scheme

: 99-50-3
3,4-Dihydroxybenzoic acid

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C 1.2: 50 - 85 °C 2.1: water; potassium hydroxide / methanol / 4 h / 20 °C 3.1: urea / 0.5 h / 220 °C 4.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 5.1: nitric acid / acetic acid / 4 h / 0 °C 6.1: sodium dithionite / water / 3 h / 50 °C 6.2: 0.5 h / 65 °C 7.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 8.1: acetic acid / toluene / 5 h / 60 °C 9.1: toluene / 5 h / 125 °C View Scheme
Multi-step reaction with 8 steps 1.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C 1.2: 50 - 85 °C 2.1: water; potassium hydroxide / methanol / 4 h / 20 °C 3.1: urea / 0.5 h / 220 °C 4.1: phosphorus pentoxide / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Reflux 5.1: nitric acid / acetic acid / 4 h / 0 °C 6.1: sodium dithionite / water / 3 h / 50 °C 6.2: 0.5 h / 65 °C 7.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 8.1: acetic acid / toluene / 125 - 130 °C View Scheme
Multi-step reaction with 7 steps 1.1: sulfuric acid / 10 h / 40 - 80 °C 2.1: potassium tert-butylate; potassium iodide / N,N-dimethyl-formamide / 12 h / 100 °C 3.1: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness 4.1: palladium 10% on activated carbon / ethanol / 10 h / 20 °C 4.2: 20 °C 5.1: ammonium formate; triethylamine / 6 h / 160 °C 6.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 50 °C 7.1: methanol / 3 h / 20 - 30 °C 7.2: 3 h / 50 °C View Scheme

: 3943-89-3
Ethyl protocatechuate

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 50 °C 2: potassium hydroxide / ethanol; water / 3 h / 20 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C 4: triethylamine / dichloromethane / 0 - 20 °C 5: triethylamine; dmap / dichloromethane / 24 h / 20 °C 6: sodium hydroxide / methanol / 2 h / 20 °C 7: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere 8: sodium hydroxide / ethanol / 20 °C 9: ethanol / 1 h / Reflux 10: hydrogenchloride / water / 2 h / 100 - 105 °C 11: trichlorophosphate / toluene / 4 h / Reflux 12: pyridine / isopropyl alcohol / 4 h / Reflux View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetone / 64 h / Inert atmosphere; Reflux 2: acetic acid; nitric acid / 24 h / 5 °C 3: hydrogenchloride; hydrogen; platinum(IV) oxide hydrate / water; ethanol / 6 h / 2327.23 Torr 4: ammonium formate / 3 h / 160 - 165 °C / Inert atmosphere 5: pyridine; trichlorophosphate / 2.5 h / Inert atmosphere 6: pyridine / isopropyl alcohol / 4 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetone / 64 h / Inert atmosphere; Reflux 2: acetic acid; nitric acid / 24 h / 5 °C 3: hydrogenchloride; hydrogen; platinum(IV) oxide hydrate / water; ethanol / 6 h / 2327.23 Torr 4: ammonium formate / 3 h / 160 - 165 °C / Inert atmosphere 5: oxalyl dichloride; N,N-dimethyl-formamide / methanol / 1.5 h / Reflux 6: pyridine / isopropyl alcohol / 4 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1.1: potassium tert-butylate; potassium iodide / N,N-dimethyl-formamide / 12 h / 100 °C 2.1: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness 3.1: palladium 10% on activated carbon / ethanol / 10 h / 20 °C 3.2: 20 °C 4.1: ammonium formate; triethylamine / 6 h / 160 °C 5.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 50 °C 6.1: methanol / 3 h / 20 - 30 °C 6.2: 3 h / 50 °C View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: potassium hydroxide / ethanol; water / 3 h / 20 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C 4: triethylamine; dmap / dichloromethane / 24 h / 20 °C 5: sodium hydroxide / methanol / 2 h / 20 °C 6: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere 7: sodium hydroxide / ethanol / 20 °C 8: ethanol / 1 h / Reflux 9: hydrogenchloride / water / 2 h / 100 - 105 °C 10: trichlorophosphate / toluene / 4 h / Reflux 11: pyridine / isopropyl alcohol / 4 h / Reflux View Scheme
Multi-step reaction with 5 steps 1: acetic acid; nitric acid / 24 h / 5 °C 2: hydrogenchloride; hydrogen; platinum(IV) oxide hydrate / water; ethanol / 6 h / 2327.23 Torr 3: ammonium formate / 3 h / 160 - 165 °C / Inert atmosphere 4: pyridine; trichlorophosphate / 2.5 h / Inert atmosphere 5: pyridine / isopropyl alcohol / 4 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: acetic acid; nitric acid / 24 h / 5 °C 2: hydrogenchloride; hydrogen; platinum(IV) oxide hydrate / water; ethanol / 6 h / 2327.23 Torr 3: ammonium formate / 3 h / 160 - 165 °C / Inert atmosphere 4: oxalyl dichloride; N,N-dimethyl-formamide / methanol / 1.5 h / Reflux 5: pyridine / isopropyl alcohol / 4 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness 2.1: palladium 10% on activated carbon / ethanol / 10 h / 20 °C 2.2: 20 °C 3.1: ammonium formate; triethylamine / 6 h / 160 °C 4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 50 °C 5.1: methanol / 3 h / 20 - 30 °C 5.2: 3 h / 50 °C View Scheme

: C13H17ClO5

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: triethylamine; dmap / dichloromethane / 24 h / 20 °C 3: sodium hydroxide / methanol / 2 h / 20 °C 4: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere 5: sodium hydroxide / ethanol / 20 °C 6: ethanol / 1 h / Reflux 7: hydrogenchloride / water / 2 h / 100 - 105 °C 8: trichlorophosphate / toluene / 4 h / Reflux 9: pyridine / isopropyl alcohol / 4 h / Reflux View Scheme

Yield

Multi-step reaction with 9 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: triethylamine; dmap / dichloromethane / 24 h / 20 °C
3: sodium hydroxide / methanol / 2 h / 20 °C
4: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere
5: sodium hydroxide / ethanol / 20 °C
6: ethanol / 1 h / Reflux
7: hydrogenchloride / water / 2 h / 100 - 105 °C
8: trichlorophosphate / toluene / 4 h / Reflux
9: pyridine / isopropyl alcohol / 4 h / Reflux
View Scheme

: C15H23NO6

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: triethylamine; dmap / dichloromethane / 24 h / 20 °C 2: sodium hydroxide / methanol / 2 h / 20 °C 3: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere 4: sodium hydroxide / ethanol / 20 °C 5: ethanol / 1 h / Reflux 6: hydrogenchloride / water / 2 h / 100 - 105 °C 7: trichlorophosphate / toluene / 4 h / Reflux 8: pyridine / isopropyl alcohol / 4 h / Reflux View Scheme

Yield

Multi-step reaction with 8 steps
1: triethylamine; dmap / dichloromethane / 24 h / 20 °C
2: sodium hydroxide / methanol / 2 h / 20 °C
3: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere
4: sodium hydroxide / ethanol / 20 °C
5: ethanol / 1 h / Reflux
6: hydrogenchloride / water / 2 h / 100 - 105 °C
7: trichlorophosphate / toluene / 4 h / Reflux
8: pyridine / isopropyl alcohol / 4 h / Reflux
View Scheme

: 2-(3,4-bis(2-methoxyethoxy)phenyl)-4,5-dihydro-oxazole

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere 2: sodium hydroxide / ethanol / 20 °C 3: ethanol / 1 h / Reflux 4: hydrogenchloride / water / 2 h / 100 - 105 °C 5: trichlorophosphate / toluene / 4 h / Reflux 6: pyridine / isopropyl alcohol / 4 h / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 40 °C / Inert atmosphere
2: sodium hydroxide / ethanol / 20 °C
3: ethanol / 1 h / Reflux
4: hydrogenchloride / water / 2 h / 100 - 105 °C
5: trichlorophosphate / toluene / 4 h / Reflux
6: pyridine / isopropyl alcohol / 4 h / Reflux
View Scheme

: C17H21F3N2O6

: 183321-74-6
erlotinib

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide / ethanol / 20 °C 2: ethanol / 1 h / Reflux 3: hydrogenchloride / water / 2 h / 100 - 105 °C 4: trichlorophosphate / toluene / 4 h / Reflux 5: pyridine / isopropyl alcohol / 4 h / Reflux View Scheme

: 183321-74-6
erlotinib

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 0℃; for 1h; Product distribution / selectivity; Inert atmosphere;	100%
With hydrogenchloride In ethanol; water at 72℃; for 0.333333h; Solvent; Temperature;	99%
With hydrogenchloride In water; acetone at 10℃; for 2.5h; Solvent; Temperature;	98.7%

: 183321-74-6
erlotinib

: N‐(3‐ethynylphenyl)‐6,7‐bis(2‐methoxyethoxy)quinazolin‐4‐amine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane at 15 - 30℃; for 3.08333h; Product distribution / selectivity;	100%
With hydrogenchloride In 1,4-dioxane; isopropyl alcohol at 0 - 70℃; for 1.5h; Solvent; Temperature;	97.2%
With hydrogenchloride In water; butanone at 30 - 35℃;	93.13%
With hydrogenchloride In isopropyl alcohol at 20 - 65℃; for 1h; Time; Concentration;	30.0 g
With hydrogenchloride In diethyl ether; chloroform	90 mg

: 79-43-6
dichloro-acetic acid

: 183321-74-6
erlotinib

: 1355242-84-0
erlotinib dichloroacetate

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 25℃; for 0.0416667h; Product distribution / selectivity;	95.43%

: 3,3-difluoro-2-iododec-1-ene

: 183321-74-6
erlotinib

: N-(3-(4,4-difluoro-3-methyleneundec-1-yn-1-yl)phenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 40℃; for 48h; Inert atmosphere;	95%

: 86520-52-7
2-[2-(2-azidoethoxy)ethoxy]ethanol

: 183321-74-6
erlotinib

: 1454772-95-2
C28H36N6O7

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In ethanol; water at 20℃; for 24h;	93%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; ethanol; water at 20℃; for 24h;	93%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; tert-butyl alcohol at 40℃; for 5h; Inert atmosphere;	54%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; tert-butyl alcohol at 60℃; for 3h; Inert atmosphere;

: 86770-67-4
2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol

: 183321-74-6
erlotinib

: C30H40N6O8

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; tert-butyl alcohol at 60℃; for 3h; Inert atmosphere;	91%

: 129392-84-3
tert-butyl N-(3-azidopropyl)carbamate

: 183321-74-6
erlotinib

: tert-butyl-3-(4-(3-(6,7-bis(2-methoxyethoxy)quinazolin-4-ylamino)phenyl)-1H-1,2,3-triazol-1-yl)propylcarbamate

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 60℃; Inert atmosphere;	90%

: 2-azidoethanesulfonyl fluoride

: 183321-74-6
erlotinib

: 2-(4-(3-((6,7-bis(2-methoxyethoxy)quinazolin-4-yl)amino)phenyl)-1H-1,2,3-triazol-1-yl)ethane-1-sulfonyl fluoride

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dimethyl sulfoxide at 20℃; for 12h;	90%

: C54H55BF2I2N8O7

: 183321-74-6
erlotinib

: C76H78BF2I2N11O11

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In ethanol; chloroform; water for 24h; Darkness;	89%

: 622-79-7
benzyl azide

: 183321-74-6
erlotinib

: N-(3-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine

Conditions

Conditions	Yield
With [(1-phenylisoquinoline)2Ir(acetylacetonate)] In dichloromethane at 20℃; Irradiation; regioselective reaction;	87%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; tert-butyl alcohol at 70℃;	0.41 g

: 201230-82-2
carbon monoxide

: 2-(2-(1-phenylethylidene)hydrazinyl)pyridine

: 183321-74-6
erlotinib

: 2-{3-[6,7-bis(2-methoxyethoxy)quinazolin-4-ylamino]phenyl}-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With dimanganese decacarbonyl In toluene at 100℃; under 760.051 Torr; for 16h; Schlenk technique; Sealed tube;	86%

...Expand

: N′-methyl-N′-(pyridin-2-yl)benzohydrazide

: 183321-74-6
erlotinib

: 3-{3-([6,7-bis(2-methoxyethoxy)quinazolin-4-yl]amino)phenyl}-2-(methyl(pyridin-2-yl)amino)isoquinolin-1(2H)-one

Conditions

Conditions	Yield
With cobalt(II) acetate; sodium pivalate at 23℃; for 16h; Inert atmosphere; Electrolysis;	85%

: 183321-74-6
erlotinib

: 13992-25-1
1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

: N-(3-(1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl)phenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol for 24h;	83%

: C46H49BF2I2N8O7

: 183321-74-6
erlotinib

: C90H95BF2I2N14O15

Conditions

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In ethanol; chloroform; water for 24h; Darkness;	82%

Erlotinib Specification

1. Introduction of Erlotinib

Erlotinib, with the IUPAC Name of N-(3-Ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine, is one kind of white or off-white crystalline powder. Its classification code are Enzyme Inhibitors and Protein Kinase Inhibitors. And it belongs to the Product Categories which include Erlotinib; Pharmaceutical intermediate. Erlotinib is used to be a antineoplastic drug.

2. Properties of Erlotinib

(1)Molecular Weight: 393.435720 g/mol; (2)Molar Refractivity: 110.06 cm³; (3)Molar Volume: 315.4 cm³; (4)Density: 1.24 g/cm³; (5)Flash Point: 288.6 °C ; (6)Index of Refraction: 1.614; (7)Polarizability: 43.63×10^-24cm³ ; (8)Surface Tension: 59.9 dyne/cm ; (9)Enthalpy of Vaporization: 83.44 kJ/mol ; (10)Boiling Point: 553.6 °C at 760 mmHg ; (11)Vapour Pressure: 2.69E-12 mmHg at 25°C。

3. Structure Descriptors of Erlotinib

You could convert the following datas into the molecular structure:
(1).Canonical SMILES: COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC
(2).InChI: InChI=1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)
(3).InChIKey: AAKJLRGGTJKAMG-UHFFFAOYSA-N

Product Name

Erlotinib

Synthetic route

Erlotinib Specification

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