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erlotinib hydrochloride
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Erlotinib hydrochloride CAS:183319-69-9
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183319-69-9 Usage

Description

Erlotinib, launched as once daily oral treatment for patients with non-small-cell lung cancer (NSCLC), is an inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase, and it is the second small-molecule drug to be marketed with this mechanism of action. Both erlotinib and its predecessor, gefitinib, are members of the anilinoquinazoline class of tyrosine kinase inhibitors. They compete with the binding of ATP to the intracellular tyrosine kinase domain of EGFR, thereby inhibiting receptor autophosphorylation and blocking downstream signal transduction. Erlotinib is prepared by the condensation of 3-ethynylaniline with 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline, which is a key intermediate obtained in five synthetic steps starting from ethyl 3,4- dihydroxybenzoate. In vitro, Erlotinib inhibits purified human EGFR tyrosine kinase with an IC50 of 2 nM and blocks EGFR autophosphorylation in cellular assays with an IC50 of 20nM. Treatment of human colon cancer cells with erlotinib was associated with growth inhibition, G1 cell cycle arrest, and apoptosis. Oral administration of erlotinib in athymic mice produced potent antitumor effects with an ED50 of 9.2 mg/kg/day for HN5 head and neck xenografts and 14 mg/ kg/day for A431 epidermoid xenografts. The absorption of Erlotinib following oral dosing is approximately 60%. Food greatly enhances the absorption allowing for almost 100% bioavailability of the dose. The time to reach peak plasma levels of the drug is about 4 hours, and the half-life is approximately 36 hours. Steady-state drug levels are reached in 7 to 8 days. Erlotinib has high protein binding (93%) and has an apparent volume of distribution of 232 L. It is metabolized primarily by CYP3A4 and to a lesser extent by CYP1A2 and CYP1A1. The drug is mainly excreted in the feces with less than 9% of the dose found in the urine. Erlotinib is labeled for the treatment of patients with locally advanced or metastatic NSCLC who have failed one or more previous chemotherapy regimens. The recommended dosage is 150 mg daily until disease progression is detected. In a randomized, double blind, placebo-controlled trial involving 731 patients, 150 mg/day oral dose of erlotinib resulted in a median overall survival of 6.7 months compared with 4.7 months in the placebo group (p<0.001). Progression-free survival was 9.9 weeks and 7.9 weeks in the erlotinib and placebo groups, respectively (p<0.001). Survival at one year was 31.2% in the erlotinib group versus 21.5% in the placebo group. The use of erlotinib showed greater benefit in patients with EGFR positive tumors and in those who never smoked. The most common adverse events reported in clinical trials were rash (9%) and diarrhea (6%). Elevations in liver function tests were also seen; however, these effects were mainly transient or associated with liver metastases. As previously noted for gefitinib, erlotinib is also shown to lack any clinical benefit in concurrent administration with platinum-based chemotherapy.

General Description

Erlotinib is available as 25-, 100-, and 150-mg tablets fororal administration and is used after failure of first-linetherapy in metastatic NSCLC and as first-line therapy incombination with gemcitabine in the treatment of metastaticpancreatic cancer, and in treating malignant gliomas.The structural similarity to gefitnib imparts similar pharmacokineticbehavior with bioavailability of 60% and proteinbinding of 93%. The agent is extensively metabolizedprimarily by CYP3A4. Three major metabolic pathwayshave been identified, involving oxidative-O-demethylationof the side chains followed by further oxidation to give thecarboxlic acids, oxidation of the acetylene functionalityto give a carboxylic acid, and aromatic hydroxylation ofthe phenyl ring para to the electron-donating nitrogen. Themetabolites are primarily eliminated in the feces, and theterminal half-life is 36 hours.The major toxicities seenwith the agent are dose-limiting skin rash and diarrhea.Other common adverse effects include shortness of breath,fatigue, and nausea.

Chemical Properties

Off-White Solid

Mechanisms of Action

The small molecular compound erlotinib is a tyrosine kinase receptor inhibitor which inhibits the proliferation of tumor cells by inhibiting phosphorylation, binding to the intracellular catalytic domain of tyrosine kinase in competition with ATP, thus blocking downstream signal transduction and inhibiting activity of tumor cell ligand dependent HER-1/EGFR.

Uses

Erlotinib HCl is an HER1/EGFR inhibitor with IC50 of 2 nM.

Uses

Erlotinib hydrochloride (V), a quinazoline derived small molecule inhibitor of epidermal growth factor receptor (EDGFR) tyrosine kinase, was approved in November, 2004, for the treatment of advanced or metastatic non-smallcell lung cancer. It belongs to the same class as gefitinib,another quinazoline approved for treatment of advanced lung cancer, but with improved pharmacokinetic properties. The molecule was originated by Pfizer and development initiated in collaboration with OSI, which assumed full rights to the drug when Pfizer merged with Warner Lambert. Subsequently, Genentech/Roche went into licensing agreement with OSI to develop and market the drug in the US and Worldwide.

Clinical Research

Phase I clinical trials showed that the main toxicities and side effects of erlotinib were dose-dependent rashes and diarrhea. Other rare side effects included headaches, nausea, and vomiting. Phase II trials used erlotinib as a second-line anticancer drug, with efficacy matching second-line chemotherapy drug docetaxel. Phase III randomized control trials (BR21) mainly focused on NSCLC patients (locally advanced and distant metastasis) after the failure of first- or second-line chemotherapy. The treatment group, with 488 cases in total, took 150mg of erlotinib daily. The control group (243 cases) took a placebo. The study showed: Median survival rate: 6.7 months for the treatment group, 4.7 months for the control (P<0.001, hazard ratio HR=0.73) 1 year survival rate: 31.2% for the treatment group, 21.5% for the control Median time of no progression: 9.9 weeks for the treatment group, 7.9 weeks for the control Meanwhile, symptomatic improvement in the treatment group was more pronounced. Based on the results of the BR21 study, several further phase III clinical trials were conducted. The TRIBUTE trial combined erlotinib with chemotherapy. The treatment group used chemotherapy (carboplatin + paclitaxel) + erlotinib, while the control used the same chemotherapy alone, with a total of 1,059 late-stage NSCLC patients. The effectiveness of the treatment group was 21.5%, and the control group 19.3%; median survival times were 10.8 and 10.6 months, respectively, and the times of tumor progression (TTP) were 5.1 and 5.0 months. Meanwhile, TALENT trials, with 1,172 NSCLC patients, also investigated the effects of adding erlotinib to chemotherapy (gemcitabine + cisplatin), and also failed to show that erlotinib significantly increased its effects.

Brand name

Tarceva (OSI).

Uses

Selective epidermal growth factor receptor (EGFR)-tyrosine kinase inhibitor. Antineoplastic

Uses

Erlotinib HCl (OSI-744) is an EGFR inhibitor with IC50 of 2 nM, >1000-fold more sensitive for EGFR than human c-Src or v-Abl. Phase 3.

Definition

ChEBI: A quinazoline hydrochloride compound having a (3-ethynylphenyl)amino group at the 4-position and two 2-methoxyethoxy groups at the 6- and 7-positions.

Originator

Pfizer (US)

Indications and Usage

Erlotinib hydrochlorate is a small molecule tyrosine kinase inhibitor which acts reversibly on epidermal growth factor receptors, a hydrochloride of erlotinib, a molecular-targeted drug. The US Food and Drug Administration (FDA) has approved erlotinib (Tarceva) combined with gemcitabine as a first-line treatment for locally advanced and metastatic pancreatic cancer. It is mainly used as a second- or third-line treatment for locally advanced or metstatic non-small cell lung cancer (NSCLC) and as a treatment for pancreatic cancer. It is used as a tyrosine inhibitor for NSCLC treatment.

Chemical Synthesis

The synthesis of this agent is based on the original patent and is shown in the Scheme. The 3,4-dihydroxy benzoate 31 was reacted with bromoethyl methyl ether in the presence of potassium carbonate and tetrabutyl ammonium iodide to give 32 in 93% yield. Nitration followed by hydrogenation provided 34 in 88% yield, which was then cyclized in formamide with ammonium formate to provide quinazolone 35. Subsequent reaction with oxalyl chloride gave quinazoline chloride 36, which was then reacted with 3-ethynyl aniline (37) in isopropanol in the presence of pyridine to give the desired product erlotinib, which was isolated as the HCl salt (V). An alternate synthesis, that used protected 3-trimethylsilyl ethynyl aniline to couple to the quinazoline chloride 36, has also been published.
InChI:InChI=1/C22H23N3O4.ClH/c1-4-16-5-7-17(8-6-16)25-22-18-13-20(28-11-9-26-2)21(29-12-10-27-3)14-19(18)23-15-24-22;/h1,5-8,13-15H,9-12H2,2-3H3,(H,23,24,25);1H

183319-69-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name erlotinib hydrochloride

1.2 Other means of identification

Product number -
Other names ERLOTINIB HCL SALT

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:183319-69-9 SDS

183319-69-9Synthetic route

erlotinib
183321-74-6

erlotinib

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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%
6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline
1312937-41-9

6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline

hydrochloric salt of m-aminophenylacetylene

hydrochloric salt of m-aminophenylacetylene

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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%
3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

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

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

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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%
6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline
1312937-41-9

6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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%
N-(3-ethynylphenyl)-6,7-dihydroxy-4-quinazolinamine
938185-06-9

N-(3-ethynylphenyl)-6,7-dihydroxy-4-quinazolinamine

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

2-iodo-1-methoxyethane

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
for 3h; Temperature; Reflux; Large scale;95.1%
4-(methylthio)-6,7-bis(2-methoxyethoxy)quinazoline
958669-57-3

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

hydrochloric salt of m-aminophenylacetylene

hydrochloric salt of m-aminophenylacetylene

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
With 3-ethynylaniline In isopropyl alcohol for 15h; Heating;90%
N-(3-trimethylsilyl-ethynyl)-6,7-bis(2-methoxyethoxy)-4-quinolyl-amine
766497-25-0

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

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 1h;90%
3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

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

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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%
2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile
950596-58-4

2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

4-(dimethoxymethylene)morpholine

4-(dimethoxymethylene)morpholine

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

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

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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
C13H19NO5
1006377-63-4

C13H19NO5

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

3,4-bis(2-methoxyethoxy) benzonitrile

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

2-nitro-4,5-bis(2-methoxyethoxy)benzonitrile

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

3,4-bis(2-methoxyethoxy)benzaldehyde

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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
3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

2-methyl-4-(3-aminophenyl)-3-butyn-2-ol

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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
3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

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

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

B

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
In isopropyl alcohol for 1.5 - 2h; Product distribution / selectivity; Heating / reflux;
2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile
950596-58-4

2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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;
erlotinib trifluoroacetate
1246445-24-8

erlotinib trifluoroacetate

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 25 - 30℃; Product distribution / selectivity;
4-(methylthio)-6,7-bis(2-methoxyethoxy)quinazoline
958669-57-3

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

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

hydrochloric salt of m-aminophenylacetylene

hydrochloric salt of m-aminophenylacetylene

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
In isopropyl alcohol for 15h; Reflux;
In isopropyl alcohol for 15h; Reflux;
4-chloro-6,7-bis(2-methoxyethoxy)quinazoline
183322-18-1

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

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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
3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

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

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

A

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

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

B

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

Conditions
ConditionsYield
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℃;
methanesulfonic acid
75-75-2

methanesulfonic acid

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

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

Conditions
ConditionsYield
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
sodium docusate
577-11-7

sodium docusate

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

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

Conditions
ConditionsYield
In dichloromethane; water at 20℃;98%
erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

erlotinib
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;
water
7732-18-5

water

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

erlotinib hydrochloride monohydrate

erlotinib hydrochloride monohydrate

Conditions
ConditionsYield
In dimethyl sulfoxide at 45℃; Temperature;92.5%
maleic acid
110-16-7

maleic acid

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

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

Conditions
ConditionsYield
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%
erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

C22H25N3O5

C22H25N3O5

Conditions
ConditionsYield
With sulfuric acid at 50℃; Reagent/catalyst; Temperature; Cooling with ice;84%
Adipic acid
124-04-9

Adipic acid

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

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

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

Conditions
ConditionsYield
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%
ethylenediamine platinum(II) nitrate
50475-22-4

ethylenediamine platinum(II) nitrate

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

C24H31ClN5O4Pt

C24H31ClN5O4Pt

Conditions
ConditionsYield
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%
cis-Pt(ethylenediamine)nitrate-chloride
468724-95-0

cis-Pt(ethylenediamine)nitrate-chloride

erlotinib hydrochloride
183319-69-9

erlotinib hydrochloride

C24H31ClN5O4Pt

C24H31ClN5O4Pt

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

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