Erlotinib hydrochloride supplier

Name
Erlotinib hydrochloride
EINECS 620-491-0
CAS No. 183319-69-9
Article Data53
CAS DataBase
Density
Solubility
Melting Point 223-225 °C
Formula C₂₂H₂₄ClN₃O₄
Boiling Point 553.6 °C at 760 mmHg
Molecular Weight 429.903
Flash Point 288.6 °C
Transport Information
Appearance White or off-white powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Quinazolinamine,N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-, monohydrochloride (9CI);6,7-Bis(2-methoxyethoxy)-4-(3-ethynylanilino)quinazoline hydrochloride;CP358774;4-Quinazolinamine,N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-, hydrochloride (1:1);OSI 774;Tarceva;[6,7-Bis(2-methoxyethoxy)quinazolin-4-yl]-(3-ethynylphenyl)amine hydrochloride;Erlotinib HCl;Erlotinib hydrochloride and Intermediate;
PSA 74.73000
LogP 4.28010

Synthetic route

: 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%

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

: hydrochloric salt of m-aminophenylacetylene

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: hydrochloric salt of m-aminophenylacetylene With sec.-butyllithium In tetrahydrofuran; cyclohexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; cyclohexane at 20℃; for 15h; Stage #3: With hydrogenchloride In tetrahydrofuran; cyclohexane; water at 20℃; for 1h; Product distribution / selectivity;	100%
Stage #1: hydrochloric salt of m-aminophenylacetylene With sec.-butyllithium In tetrahydrofuran; cyclohexane at 0℃; Inert atmosphere; Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; cyclohexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; cyclohexane; water at 20℃;	100%

: 54060-30-9
3-acetylenephenylamine

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

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
In isopropyl alcohol for 18h; Heating;	98%
In iso-propanol (IPA) for 0.5h; Product distribution / selectivity; Heating / reflux;	97%
Stage #1: 3-acetylenephenylamine; 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline In N,N-dimethyl-formamide; acetonitrile at 90℃; for 7h; Darkness; Stage #2: With hydrogenchloride In water at 15 - 30℃; Temperature; Solvent;	97.6%

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

: 54060-30-9
3-acetylenephenylamine

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-acetylenephenylamine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; for 0.5h; Inert atmosphere; Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; for 15h; Stage #3: With hydrogenchloride In tetrahydrofuran; n-heptane; ethylbenzene; water at 20℃; for 3h; Product distribution / selectivity;	97%
Stage #1: 3-acetylenephenylamine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; Inert atmosphere; Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; for 15h; Stage #3: With hydrogenchloride In tetrahydrofuran; n-heptane; ethylbenzene; water at 20℃; Product distribution / selectivity;	97%

Yield

Stage #1: 3-acetylenephenylamine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; for 15h;
Stage #3: With hydrogenchloride In tetrahydrofuran; n-heptane; ethylbenzene; water at 20℃; for 3h; Product distribution / selectivity;

97%

Stage #1: 3-acetylenephenylamine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 0℃; Inert atmosphere;
Stage #2: 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; for 15h;
Stage #3: With hydrogenchloride In tetrahydrofuran; n-heptane; ethylbenzene; water at 20℃; Product distribution / selectivity;

97%

: 938185-06-9
N-(3-ethynylphenyl)-6,7-dihydroxy-4-quinazolinamine

: 4296-15-5
2-iodo-1-methoxyethane

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: N-(3-ethynylphenyl)-6,7-dihydroxy-4-quinazolinamine; 2-iodo-1-methoxyethane With pyridine; tetrapropylammonium iodide In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; Stage #2: With hydrogenchloride In water	95.29%

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

: 54060-30-9
3-acetylenephenylamine

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
for 3h; Temperature; Reflux; Large scale;	95.1%

: 958669-57-3
4-(methylthio)-6,7-bis(2-methoxyethoxy)quinazoline

: hydrochloric salt of m-aminophenylacetylene

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
With 3-ethynylaniline In isopropyl alcohol for 15h; Heating;	90%

: 766497-25-0
N-(3-trimethylsilyl-ethynyl)-6,7-bis(2-methoxyethoxy)-4-quinolyl-amine

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 1h;	90%

: 54060-30-9
3-acetylenephenylamine

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 6,7-dimethoxy quinazolin-4-one With triethylamine; trichlorophosphate In toluene at 70 - 80℃; for 3h; Stage #2: 3-acetylenephenylamine In toluene; acetonitrile at 20 - 80℃; for 2h;	88%

: 299912-59-7
3-butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl, hydrochloride

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl, hydrochloride With sodium hydroxide In water; butan-1-ol pH=10 - 12; Inert atmosphere; Stage #2: With sodium hydroxide In butan-1-ol at 115 - 120℃; for 24h; Stage #3: With hydrogenchloride In water; butan-1-ol at 20 - 25℃;	74%

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

: 54060-30-9
3-acetylenephenylamine

: 4-(dimethoxymethylene)morpholine

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-acetylenephenylamine; 4-(dimethoxymethylene)morpholine With acetic acid In toluene Reflux; Stage #2: 2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile In toluene Reflux; Stage #3: With hydrogenchloride In water; toluene at 15 - 20℃;	63%

...Expand

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

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 95 percent / P2S5 / pyridine / 24 h / Heating 2.1: aq. NaOH / methanol / 0.5 h / 20 °C 2.2: 86 percent / methanol; H2O / 5 h / 25 °C 3.1: 90 percent / 3-ethynylaniline / propan-2-ol / 15 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 2: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C 2: pyridine / propan-2-ol View Scheme

: 958669-56-2
6,7-bis(2-methoxyethoxy)quinazoline-4(3H)-thione

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aq. NaOH / methanol / 0.5 h / 20 °C 1.2: 86 percent / methanol; H2O / 5 h / 25 °C 2.1: 90 percent / 3-ethynylaniline / propan-2-ol / 15 h / Heating View Scheme

: 1006377-63-4
C13H19NO5

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: acetic anhydride / 110 °C 2.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 3.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 3.2: 81 percent / HCl / H2O / 90 - 130 °C 4.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 5.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme

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

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 2.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 2.2: 81 percent / HCl / H2O / 90 - 130 °C 3.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 4.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme
Multi-step reaction with 6 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 6.1: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme
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 / 125 - 130 °C 5.1: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme
Multi-step reaction with 5 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 5.1: hydrogenchloride / water; methanol / 20 °C View Scheme
Multi-step reaction with 6 steps 1: nitric acid 2: dihydrogen peroxide 3: palladium on activated charcoal; ammonium formate 4: water / 24 h / 130 °C 5: trichlorophosphate; triethylamine 6: hydrogenchloride / water; N,N-dimethyl-formamide View Scheme

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

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 1.2: 81 percent / HCl / H2O / 90 - 130 °C 2.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 3.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme
Multi-step reaction with 5 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 5.1: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme
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 / 125 - 130 °C 4.1: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme

: 80407-64-3
3,4-bis(2-methoxyethoxy)benzaldehyde

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: hydroxylamine hydrochloride; pyridine / methanol / Heating 2.1: acetic anhydride / 110 °C 3.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 4.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 4.2: 81 percent / HCl / H2O / 90 - 130 °C 5.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 6.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme
Multi-step reaction with 7 steps 1: hydroxylamine hydrochloride; acetic anhydride 2: nitric acid 3: dihydrogen peroxide 4: palladium on activated charcoal; ammonium formate 5: water / 24 h / 130 °C 6: trichlorophosphate; triethylamine 7: hydrogenchloride / water; N,N-dimethyl-formamide View Scheme

Yield

Multi-step reaction with 6 steps
1.1: hydroxylamine hydrochloride; pyridine / methanol / Heating
2.1: acetic anhydride / 110 °C
3.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
4.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
4.2: 81 percent / HCl / H2O / 90 - 130 °C
5.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating
6.1: 80 percent / dimethylformamide / 1 h / 80 °C
View Scheme

Multi-step reaction with 7 steps
1: hydroxylamine hydrochloride; acetic anhydride
2: nitric acid
3: dihydrogen peroxide
4: palladium on activated charcoal; ammonium formate
5: water / 24 h / 130 °C
6: trichlorophosphate; triethylamine
7: hydrogenchloride / water; N,N-dimethyl-formamide
View Scheme

: 139-85-5
3,4-dihydroxybenzaldehyde

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 98 percent / potassium carbonate / dimethylformamide / 100 °C 2.1: hydroxylamine hydrochloride; pyridine / methanol / Heating 3.1: acetic anhydride / 110 °C 4.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 5.2: 81 percent / HCl / H2O / 90 - 130 °C 6.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 7.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 98 percent / potassium carbonate / dimethylformamide / 100 °C
2.1: hydroxylamine hydrochloride; pyridine / methanol / Heating
3.1: acetic anhydride / 110 °C
4.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
5.2: 81 percent / HCl / H2O / 90 - 130 °C
6.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating
7.1: 80 percent / dimethylformamide / 1 h / 80 °C
View Scheme

: 3943-89-3
Ethyl protocatechuate

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: potassium carbonate; tetrabutylammonium iodide / acetone / 120 h / Heating 2: acetic acid; nitric acid / 24 h / 20 °C 3: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 4: 84 percent / 12 h / 165 - 170 °C 5: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C 6: pyridine / propan-2-ol View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate; tetrabutylammonium iodide / acetone 2: acetic acid; nitric acid / 24 h / 20 °C 3: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 4: 84 percent / 12 h / 165 - 170 °C 5: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C 6: pyridine / propan-2-ol View Scheme
Multi-step reaction with 7 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 7.1: hydrogenchloride / water; dichloromethane; methanol / 3 h / 25 °C View Scheme

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

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic acid; nitric acid / 24 h / 20 °C 2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 3: 84 percent / 12 h / 165 - 170 °C 4: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C 5: pyridine / propan-2-ol View Scheme
Multi-step reaction with 6 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 6.1: hydrogenchloride / water; dichloromethane; methanol / 3 h / 25 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: acetic acid; nitric acid / 24 h / 20 °C
2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr
3: 84 percent / 12 h / 165 - 170 °C
4: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C
5: pyridine / propan-2-ol
View Scheme

Multi-step reaction with 6 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
6.1: hydrogenchloride / water; dichloromethane; methanol / 3 h / 25 °C
View Scheme

: 179688-27-8
ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / 12 h / 165 - 170 °C 2: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C 3: pyridine / propan-2-ol View Scheme

: 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 2: 84 percent / 12 h / 165 - 170 °C 3: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C 4: pyridine / propan-2-ol View Scheme
Multi-step reaction with 4 steps 1.1: tin(II) chloride dihdyrate / methanol / 25 - 35 °C 1.2: 0 - 30 °C 2.1: 25 - 145 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux 4.1: isopropyl alcohol / 4 h / 25 - 45 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: palladium 10% on activated carbon / ethanol / 10 h / 20 °C 1.2: 20 °C 2.1: ammonium formate; triethylamine / 6 h / 160 °C 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 50 °C 4.1: methanol / 3 h / 20 - 30 °C 4.2: 3 h / 50 °C 5.1: hydrogenchloride / water; dichloromethane; methanol / 3 h / 25 °C View Scheme

: 69088-96-6
2-methyl-4-(3-aminophenyl)-3-butyn-2-ol

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / toluene / 1 h / Heating 2: 98 percent / propan-2-ol / 18 h / Heating View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene / 4 h / 105 - 110 °C / Inert atmosphere 2: toluene; acetonitrile / 25 °C / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1.1: acetonitrile / 5 h / 25 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / butan-1-ol; water / pH 10 - 12 / Inert atmosphere 2.2: 24 h / 115 - 120 °C 2.3: 20 - 25 °C View Scheme
Multi-step reaction with 2 steps 1: acetonitrile / 5 h / Inert atmosphere; Reflux 2: sodium hydroxide; water / butan-1-ol / pH 10 - 12 / Inert atmosphere View Scheme

: 54060-30-9
3-acetylenephenylamine

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

A: N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-N-(2-methoxyethyl)quinazolin-4-amine

B: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
In isopropyl alcohol for 1.5 - 2h; Product distribution / selectivity; Heating / reflux;

...Expand

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

: 54060-30-9
3-acetylenephenylamine

: 122-51-0
orthoformic acid triethyl ester

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile; 3-acetylenephenylamine; orthoformic acid triethyl ester; acetic acid In isopropyl alcohol for 4h; Reflux; Stage #2: With hydrogenchloride In isopropyl alcohol at 20℃; pH=3.0 - 4.0; Product distribution / selectivity;

...Expand

: 1246445-24-8
erlotinib trifluoroacetate

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 25 - 30℃; Product distribution / selectivity;

: 958669-57-3
4-(methylthio)-6,7-bis(2-methoxyethoxy)quinazoline

: 54060-30-9
3-acetylenephenylamine

: hydrochloric salt of m-aminophenylacetylene

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
In isopropyl alcohol for 15h; Reflux;
In isopropyl alcohol for 15h; Reflux;

...Expand

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

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridine / isopropyl alcohol / 1 h / 80 °C 1.2: 1 h / 20 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 0.5 h / 80 °C 2.2: 0.5 h / 0 - 40 °C 3.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 0.5 h / 0 °C / Inert atmosphere 3.2: 15 h / 20 °C 3.3: 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: pyridine / isopropyl alcohol / 1 h / 80 °C 1.2: 1 h / 20 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 0.5 h / 80 °C 2.2: 0.5 h / 0 - 40 °C 3.1: sec.-butyllithium / cyclohexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 15 h / 20 °C 3.3: 1 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: pyridine / isopropyl alcohol / 1 h / 80 °C 1.2: 20 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 0.5 h / 80 °C 2.2: 0 - 40 °C 3.1: sec.-butyllithium / cyclohexane; tetrahydrofuran / 0 °C / Inert atmosphere 3.2: 20 °C 3.3: 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: pyridine / isopropyl alcohol / 1 h / 80 °C 1.2: 20 °C 2.1: trichlorophosphate / N,N-dimethyl-formamide / 0.5 h / 80 °C 2.2: 0 - 40 °C 3.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 0 °C / Inert atmosphere 3.2: 15 h / 20 °C 3.3: 20 °C View Scheme
With hydrogenchloride In water; N,N-dimethyl-formamide

: 54060-30-9
3-acetylenephenylamine

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

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

B: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-acetylenephenylamine; 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline With pyridine In isopropyl alcohol at 80℃; for 1h; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether; chloroform at 20℃; for 1h; Product distribution / selectivity;
Stage #1: 3-acetylenephenylamine; 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline With pyridine In isopropyl alcohol at 80℃; for 1h; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether; chloroform at 20℃;

...Expand

: 75-75-2
methanesulfonic acid

: 183319-69-9
erlotinib hydrochloride

: N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine, methanesulfonic acid salt

Conditions

Conditions	Yield
Stage #1: erlotinib hydrochloride With sodium hydroxide In water; ethyl acetate at 60 - 70℃; pH=10 - 11; Stage #2: methanesulfonic acid In ethyl acetate Heating / reflux;	100%
Stage #1: erlotinib hydrochloride With sodium hydroxide In water; ethyl acetate pH=8 - 9; Stage #2: In isopropyl alcohol Stage #3: methanesulfonic acid at 62 - 70℃; for 34h;	93%
Stage #1: erlotinib hydrochloride With sodium hydrogencarbonate In dichloromethane; water Stage #2: In isopropyl alcohol Stage #3: methanesulfonic acid	69%
Stage #1: erlotinib hydrochloride With 50percent NaOH In water; ethyl acetate at 50℃; for 0.25h; Stage #2: methanesulfonic acid at 50℃; for 4h; Further stages.;	111.76 g

: 577-11-7
sodium docusate

: 183319-69-9
erlotinib hydrochloride

: erlotinib 1,4-bis(2-ethylhexoxy)-1 ,4-dioxobutane-2-sulfonate

Conditions

Conditions	Yield
In dichloromethane; water at 20℃;	98%

: 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;

: 7732-18-5
water

: 183319-69-9
erlotinib hydrochloride

: erlotinib hydrochloride monohydrate

Conditions

Conditions	Yield
In dimethyl sulfoxide at 45℃; Temperature;	92.5%

: 110-16-7
maleic acid

: 183319-69-9
erlotinib hydrochloride

: [6,7-bis(2-methoxyethoxy)-4-chinazolinyl](3-ethynylphenyl)amine maleate

Conditions

Conditions	Yield
Stage #1: erlotinib hydrochloride With ammonium hydroxide In water; ethyl acetate at 50℃; for 0.5h; Stage #2: maleic acid In ethanol; ethyl acetate at 20℃; for 24h;	89%

: 183319-69-9
erlotinib hydrochloride

: C22H25N3O5

Conditions

Conditions	Yield
With sulfuric acid at 50℃; Reagent/catalyst; Temperature; Cooling with ice;	84%

: 124-04-9
Adipic acid

: 183319-69-9
erlotinib hydrochloride

: 1429636-54-3
[6,7-bis(2-methoxyethoxy)-4-chinazolinyl](3-ethynylphenyl)amine adipinate

Conditions

Conditions	Yield
Stage #1: erlotinib hydrochloride With ammonium hydroxide In water; ethyl acetate at 50℃; for 0.5h; Stage #2: Adipic acid In ethanol; ethyl acetate for 24h; Cooling with ice;	72%

: 50475-22-4
ethylenediamine platinum(II) nitrate

: 183319-69-9
erlotinib hydrochloride

: C24H31ClN5O4Pt

Conditions

Conditions	Yield
Stage #1: erlotinib hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: ethylenediamine platinum(II) nitrate In N,N-dimethyl-formamide at 65℃; for 17h;	29%

: 468724-95-0
cis-Pt(ethylenediamine)nitrate-chloride

: 183319-69-9
erlotinib hydrochloride

: C24H31ClN5O4Pt

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 65℃; for 17h;	22%

Erlotinib hydrochloride Specification

1. Introduction of Erlotinib hydrochloride

Erlotinib hydrochloride, with the IUPAC Name of N-(4-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine hydrochloride, is one kind of white crystalline powder, odorless, little bitter taste. This product belongs to the Product Categories which include API; Molecular Targeted Antineoplastic; Heterocyclic Compounds; anti-neoplastic; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals.

2. Properties of Erlotinib hydrochloride

Erlotinib hydrochloride has the following datas: (1)Flash Point: 288.6 °C; (2)Enthalpy of Vaporization: 83.44 kJ/mol; (3)Melting Point: 223-225°C; (4)Boiling Point: 553.6 °C at 760 mmHg; (5)Vapour Pressure: 2.69E-12 mmHg at 25°C.

3. Use of Erlotinib hydrochloride

Erlotinib hydrochloride (CAS NO.183319-69-9) is a drug used to treat non-small cell lung cancer, pancreatic cancer and several other types of cancer.

Product Name

Erlotinib hydrochloride

Synthetic route

Erlotinib hydrochloride Specification

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