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Erlotinib impurity
Cas No: 183321-74-6
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High purity Various Specifications Erlotinib CAS:183321-74-6
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erlotinib
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Erlotinib
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Erlotinib 183321-74-6
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183321-74-6 Usage

Gefitinib

Gefitinib is an aniline quinazoline derivative and is also a selective epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor that inhibits the growth, metastasis and angiogenesis of tumors and increases tumor cell apoptosis;
Gefitinib is a kind of highly-specific anti-tumor targeted therapy drugs developed by the United Kingdom AstraZeneca, being the first molecular targeted drug for the treatment of non-small cell lung cancer. It takes effects through selectively inhibiting the signal transduction pathway of the epidermal growth factor receptor tyrosine kinase (EGFR-TK). Epidermal growth factor (EGF) is a polypeptide with a relative molecular mass of 6.45 × 103 that binds to the epidermal growth factor receptor (EGFR) on the target cell membrane to produces biological effects. EGFR is a tyrosine kinase (TK) receptor that, when conjugated to EGF, being capable of promoting the TK activation in the receptor, leading to auto-phosphorylation of the receptor tyrosine residue, providing a continuous signal splitting into the cell, further causing cell proliferation and differentiation. EGFR is abundant in human tissues and highly expressed in malignant tumors. Gefitinib, through interfering with the EGFR signaling transduction pathways on the cell surface, inhibits the tumor growth, metastasis and angiogenesis and induces tumor cell apoptosis.
In August 2002, gefitinib, as a first-line treatment of non-small cell lung cancer drugs, was first listed in Japan under the trade name of Iressa.
In May 2003, the US Food and Drug Administration approved gefitinib as the three-line monotherapy drug for patients with advanced non-small cell lung cancer that can’t be cured by platinum-based anti-cancer drugs and docetaxel chemotherapy. Now, it has been also approved by Australia, Japan, Argentina, Singapore and South Korea and other countries for the treatment of advanced non-small cell lung cancer.
On February 28, 2005, the Chinese Food and Drug Administration approved gefitinib for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) previously subjecting to chemotherapy treatment. It has not yet been approved as a first-line treatment for advanced NSCLC.
On July 1, 2009, the European Union Drug Administration has formally approved gefitinib for the first, second and third line treatment of adult EGFR mutations locally advanced or metastatic non-small cell lung cancer.

Clinical evaluation

Erlotinib is another tyrosine kinase inhibitor for the treatment of NSCLC after imatinib. The phase I clinical trial results have shown that its main toxicity and side effects are dose-dependent rash and diarrhea. Other rare side effects also include headache, nausea and vomiting.
Phase II trial takes erlotinib as a second line antineoplastic drugs with the efficacy being comparable as the second-line chemotherapy drug docetaxel. The Phase III randomized controlled trial (BR21) was performed in patients with NSCLC who had failed in the primary or secondary chemotherapy (locally advanced and distant metastases). Study group applied erlotinib in a dosage of 150mg daily for treatment of a total of 488 cases. A total of 243 cases were treated with placebo in the control group. The result: the median overall survival rate was 6.7 months in the treatment group and 4.7 months in the control group (P <0.001, HR = 0.73). The 1-year survival rate was 31.2% in the treatment group and 21.5% in the control group; the time of progression was 9.9 weeks in treatment group and 7.9 weeks in control group while the improvement of symptoms in patients with erlotinib was more obvious.
Based on the results of BR21 research, a number of phase Ⅲ clinical studies have been carried out successively. TRIBUTE clinical trial combined the Erlotinib with chemotherapy in an attempt to compare whether the efficacy of its combination with chemotherapy is better than chemotherapy alone. For the treatment group, chemotherapy (carboplatin plus paclitaxel) + erlotinib were combined; for the control group, the same chemotherapy was used alone. A total of 1059 patients with advanced NSCLC were included in the study. The efficacy in the research result: 21.5% for research group; 19.3% for the control group. The median survival time was 10.8 months in the study group and 10.6 months in the control group. The time to tumor progression (TTP) was 5.1 months in the study group and 5.0 months in the control group. Another TALENT study also focused on whether the combination of erlotinib and chemotherapy (gemcitabine + cisplatin) can improve the efficacy of chemotherapy and have included a total of 1172 cases of NSCLC patients. The results also did not show that erlotinib can significantly improve the efficacy of chemotherapy.

Uses

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

Adverse reactions and precautions

Common adverse reactions include rash, fever, anorexia, indigestion, nausea, vomiting, diarrhea, constipation and abdominal pain, fatigue, weight loss and edema, bone pain and muscle pain, dyspnea, elevated transaminases. In rare cases, it was observed of bone marrow suppression. Oral administration of warfarin may lead to unexpectedly increased international standardization ratio. There are occasionally chills, cough, stomatitis, keratoconjunctivitis, anxiety and neurological diseases, elevated bilirubin. In rare cases, there are microangiopathies hemolytic anemia and thrombocytopenia. Cough and fever may be associated with interstitial lung disease, if it occurs, the drugs should be discontinued. Cytochrome P450 enzymes affect the metabolism of the product. Its inhibitor ketoconazole or agonist rifampicin can change the plasma concentration of this product, resulting in increased toxicity or reduced toxicity. Patients of co-administration of warfarin should subject to closely monitoring of the international normalized ratio.

Molecular targeted therapy

The small molecule compound, Erlotinib is a receptor tyrosine kinase inhibitor (EGFR antagonist) and belongs to molecular targeted therapy Drugs. It can inhibit the phosphorylation reaction through competing with adenosine triphosphate to bind to the catalytic region of the receptor tyrosine kinase, thereby blocking the down-proliferation signaling and inhibiting the activity of the tumor cell ligand-dependent HER-1/EGFR, thus achieving the inhibition of the proliferation of tumor cells. Clinically, it is mainly used in the treatment of incurable locally advanced or metastatic non-small cell lung cancer (NSCLC) and being used in combination with gemcitabine for first-line treatment of locally advanced unresectable or metastatic pancreatic cancer.
In November 2004, the product was first approved in the United States for the treatment of local advanced or metastatic non-small cell lung cancer (NSCLC) which has been undergone at least one time of chemotherapy failure.
In 2005, the results of a Phase III trial of the NCI Canadian Clinical Trials Group suggested that gemcitabine, in combination with erlotinib (EGFR blocker) can increase the median survival of patients with advanced pancreatic cancer from 5.9 months to 6.4 months and 1-year survival from 17% to 24%.
In November 2005, Genentech and OSI jointly announced that the US Food and Drug Administration (FDA) had approved the combination of erlotinib (Tarceva) and gemcitabine as first-line treatment for advanced pancreatic cancer.

What is molecular targeted therapy?

Molecular targeted therapy is no longer a new term. Scientists are constantly exploring the pathogenesis of cancer molecular biology, realizing that if specific changes in cancer can be given by a powerful blow, it will greatly improve the treatment effect, triggering changes in anti-cancer treatment concept. In recent years, new molecular targeted drugs in clinical practice have achieved remarkable results. The practice has shown that the correctness and feasibility of the molecular targeted therapy theory, putting the cancer treatment to an unprecedented new stage.
Depending on the target and nature of the drug, the drugs of the major target molecule therapy can be divided into the following categories:
(1) Small molecule tyrosine kinase inhibitors of epidermal growth factor receptor (EGFR): such as gefitinib (Iressa), Erlotinib (Tarceva);
(2) anti-EGFR monoclonal antibody: such as cetuximab (Erbitux);
(3) Anti-HER-2 monoclonal antibody: such as Herceptin (Trastuzumab);
(4) Bcr-Abl tyrosine kinase inhibitors: such as imatinib;
(5) Vascular endothelial growth factor receptor inhibitors: such as Bevacizumab (Avastin);
(6) anti-CD20 monoclonal antibody: such as rituximab (Rituximab);
(7) IGFR-1 kinase inhibitors such as NVP-AEW541;
(8) mTOR kinase inhibitors: such as CCI-779;
(9) Ubiquitin-proteasome inhibitors: such as Bortezomib;
(10) Other: such as Aurora kinase inhibitors, histone deacetylase (HDACs) inhibitors.

Definition

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

Uses

A tyrosine kinase inhibitor

Dosage and Usage

Non-small cell lung cancer: 150mg/d; administrate at least1h before meals or 2h after meal; continue taking the drug until the disease get progression or the emergence of intolerable toxicity response when the patients should withdraw the drug.
Pancreatic cancer: combine with gemcitabine for 100mg /d at least 1h before meals or 2h after meals; continue taking the drug until the disease get progression or the emergence of intolerable toxicity response when the patients should withdraw the drug.
Upon severe liver insufficiency, the drug dosage should be reduced or temporarily discontinued, elderly patients do not have to adjust the dose.

Brand name

Tarceva (OSI).

Uses

antineoplastic;tyrosine kinase inhibitor
InChI:InChI=1/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)

183321-74-6SDS

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

1.2 Other means of identification

Product number -
Other names Erlotinib

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:183321-74-6 SDS

183321-74-6Synthetic route

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

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

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

erlotinib
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℃;
2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile
950596-58-4

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

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

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

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 110℃; for 5h; Temperature; Solvent;88.2%
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
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%
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
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%
3,4-bis(2-methoxyethoxy) benzonitrile
80407-68-7

3,4-bis(2-methoxyethoxy) benzonitrile

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

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

erlotinib
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

C24H30N4O4

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
In toluene at 125℃; for 5h;47 g
methoxyethoxy 3,4-bis(2-methoxyethoxy)-benzoate

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

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

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

erlotinib
183321-74-6

erlotinib

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

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

erlotinib
183321-74-6

erlotinib

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

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

erlotinib
183321-74-6

erlotinib

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

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

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / toluene / 5 h / 60 °C
2: toluene / 5 h / 125 °C
View Scheme
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
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
Ethyl protocatechuate
3943-89-3

Ethyl protocatechuate

erlotinib
183321-74-6

erlotinib

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

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

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
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

C13H17ClO5

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
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

C15H23NO6

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
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

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

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
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

C17H21F3N2O6

erlotinib
183321-74-6

erlotinib

Conditions
ConditionsYield
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
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%
erlotinib
183321-74-6

erlotinib

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

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

Conditions
ConditionsYield
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; chloroform90 mg
dichloro-acetic acid
79-43-6

dichloro-acetic acid

erlotinib
183321-74-6

erlotinib

erlotinib dichloroacetate
1355242-84-0

erlotinib dichloroacetate

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 25℃; for 0.0416667h; Product distribution / selectivity;95.43%
3,3-difluoro-2-iododec-1-ene

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

erlotinib
183321-74-6

erlotinib

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

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

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 40℃; for 48h; Inert atmosphere;95%
2-[2-(2-azidoethoxy)ethoxy]ethanol
86520-52-7

2-[2-(2-azidoethoxy)ethoxy]ethanol

erlotinib
183321-74-6

erlotinib

C28H36N6O7
1454772-95-2

C28H36N6O7

Conditions
ConditionsYield
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;
2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol
86770-67-4

2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol

erlotinib
183321-74-6

erlotinib

C30H40N6O8

C30H40N6O8

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water; tert-butyl alcohol at 60℃; for 3h; Inert atmosphere;91%
tert-butyl N-(3-azidopropyl)carbamate
129392-84-3

tert-butyl N-(3-azidopropyl)carbamate

erlotinib
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

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

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

2-azidoethanesulfonyl fluoride

erlotinib
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

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
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dimethyl sulfoxide at 20℃; for 12h;90%
C54H55BF2I2N8O7

C54H55BF2I2N8O7

erlotinib
183321-74-6

erlotinib

C76H78BF2I2N11O11

C76H78BF2I2N11O11

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In ethanol; chloroform; water for 24h; Darkness;89%
benzyl azide
622-79-7

benzyl azide

erlotinib
183321-74-6

erlotinib

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

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

Conditions
ConditionsYield
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
carbon monoxide
201230-82-2

carbon monoxide

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

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

erlotinib
183321-74-6

erlotinib

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

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

Conditions
ConditionsYield
With dimanganese decacarbonyl In toluene at 100℃; under 760.051 Torr; for 16h; Schlenk technique; Sealed tube;86%
N′-methyl-N′-(pyridin-2-yl)benzohydrazide

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

erlotinib
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

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

Conditions
ConditionsYield
With cobalt(II) acetate; sodium pivalate at 23℃; for 16h; Inert atmosphere; Electrolysis;85%
erlotinib
183321-74-6

erlotinib

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate
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

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
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol for 24h;83%
C46H49BF2I2N8O7

C46H49BF2I2N8O7

erlotinib
183321-74-6

erlotinib

C90H95BF2I2N14O15

C90H95BF2I2N14O15

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

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