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Erlotinib
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Name

Erlotinib

 EINECS 689-196-2
CAS No. 183321-74-6 Density 1.247 g/cm3
PSA 74.73000 LogP 3.47810
Solubility N/A 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 N/A Appearance white to off-white powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 183321-74-6 (Erlotinib) Hazard Symbols N/A
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;

Article Data 44

Erlotinib Synthetic route

54060-30-9

3-acetylenephenylamine

183322-18-1

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

183321-74-6

erlotinib

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

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

183321-74-6

erlotinib

Conditions
ConditionsYield
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

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

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