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High purity Various Specifications Iressa CAS:184475-35-2
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184475-35-2 Usage

Pharmacokinetics

It is orally effective, with relatively slow absorption and metabolism following intake. The bioavailability of a single oral 250mg dose is nearly 60%, and its area under curve (AUC) is dependent on dosage. With single daily dosages, blood concentration is steady after 7-10 days, with blood concentration peaking 3-7 hours after medication and then gradually following biphasic reduction (its half-life is 12-58 hours, at an average of 28 hours). It is observed as dose-dependent pharmacokinetics, and following multiple dosages, AUC and Cmax increased proportionally. When taken with food, its Cmax and AUC did not decrease significantly. Its plasma protein binding rate is nearly 90%. Gefitinib is metabolized through many different pathways in the livers in a relatively complicated process; the main component of its oxidative metabolism is the cytochrome P450 enzyme CYP3A4, which mainly metabolizes O-Desmethyl metabolites. Metabolites are unrelated to the pharmacological effects of the original drug. The original drug and many metabolites are mostly passed through the biliary tract and excreted through feces, while the amount of drug excreted through urine is less than 4% the original dosage amount.

Indications and Uses

Gefitinib is an antineoplastic target therapy drug with relatively high specificity that was developed by the British pharmaceutical company AstraZeneca; it is the first molecular targeted drug to be used in non-small cell lung cancer treatment. Epidermal growth factors (EGF) are a kind of polypeptide with a relative molecular mass of 6.45x103, and they can bind with epidermal growth factor receptors (EGFR) on target cell membrane surfaces to trigger biological effects. EGFR is a type of tyrosine kinase (TK) type receptor, so when bound with EGF, it will promote TK activation in the receptor. This will cause tyrosine residue in the receptor to autophosphorylate and send continuous dividing signals into the cell, causing cell proliferation and differentiation. EGFR is abundant in human tissue, and it is highly expressed in malign tumors. Gefitinib blocks the signal transduction pathway of cell surface EGFR to prevent tumor growth, metastasis, and growth in blood vessels, and it can induce tumor cell apoptosis. Gefitinib is mainly used to treat non-stem cell lung cancer.

Indications

The EGFR or ErbB1 inhibitor gefitinib (Iressa(R), AstraZeneca) was originally approved by the US FDA in 2003 under accelerated regulations for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) after progression on docetaxel- and platinum-based chemotherapy. AstraZeneca voluntarily withdrew gefitinib from the market in 2005, owing to failed verification of clinical benefit during post-approval studies. In July 2015, FDA reinstated the approval of gefitinib for a different group of patients (i.e., NSCLC patients with EGFR mutations). Other approved kinase inhibitors targeting the ErbB family, which includes ErbB1/EGFR, ErbB2/human epidermal growth factor receptor 2 (Her2), ErbB3/ Her3, and ErbB4/Her4, are erlotinib (Tarceva(R), OSI Pharm.), lapatinib (Tykerb(R), GlaxoSmithKline), vandetanib (Caprelsa(R), AstraZeneca), afatinib (Gilotrif(R), Boehringer Ingelheim) , and osimertinib (Tagrisso(R), AstraZeneca). All approved EGFR family inhibitors share a common quinazoline scaffold with the exception of osimertinib, which has a pyrimidinylphenylamine scaffold that resembles that of imatinib and nilotinib. Gefitinib and vandetanib adopt the type I binding mode with “DFG-in” and αC-helix “in” conformation, while erlotinib and lapatinib bind to“DFG-in”with the αC-helix adopting an “out” conformation. Afatinib and osimertinib are covalent inhibitors with an electrophilic enone moiety.

Originator

Astra Zeneca (UK)

Adverse Reactions

Gefitinib is relatively well-tolerated, and most negative reactions are mild and reversible, characteristics that are vastly different from those of standard negative reactions to cytotoxic drugs. Common negative reactions include diarrhea, nausea, rashes, acne, vomiting, and feebleness. Only 1% of patients have had to cease treatment due to negative reactions with an occurrence rate over 20%. There have also been rare cases of acute interstitial pneumonia.

Chemical Synthesis

A mixture of 4,5-dimethoxyanthranilic acid (133) and formamide was heated to generate the cyclized quinazoline 134. The quinazoline was selectively monodemethylated with methionine in refluxing methanesulfonic acid to afford 135 in 47% yield. Compound 135 was acylated to give acetate 136, which was treated with refluxing thionyl chloride to yield chloropyrimidine 137. Chloride 137 was condensed with 3-chloro-4-fluoroaniline (138) in refluxing IPA to yield anilinoquinazoline 139 in 56% yield from 136. The acetate protecting group in compound 139 was hydrolyzed with ammonium hydroxide in methanol, and the free phenol was alkylated with 3-(4- morpholinyl)propyl chloride (140) to give gefitinib (13) in 55% yield.

Uses

Gefitinib is an antineoplastic.

Chemical Properties

Light-Yellow Crystalline Powder

Uses

Gefitinib (Iressa, ZD-1839) is an EGFR inhibitor for Tyr1173, Tyr992, Tyr1173 and Tyr992 in the NR6wtEGFR and NR6W cells with IC50 of 37 nM, 37nM, 26 nM and 57 nM, respectively.

General Description

Geftinib is available as 250-mg tablets for oral administrationin the treatment of NSCLC for those patients who have failedto respond to platinum-based therapies and docetaxel and hasalso been used against squamous cell cancers of the head andneck. The agent is an inhibitor of the TK of EGF-R and possiblyother TKs as well. Gefitinib is both a substrate and inhibitorof Pgp and BCRP. The agent is absorbed slowly afterbeing administered orally with 60% bioavailability.Metabolism occurs in the liver and is mediated primarily byCYP3A4 to give eight identified metabolites resulting fromdefluorination of the phenyl ring, oxidative-O-demethylation,and multiple products arising as a result of oxidation of themorpholine ring. The O-demethylated product represents thepredominate metabolite and is 14-fold less active comparedwith the parent. The parent and metabolites are eliminated inthe feces with a terminal elimination half-life of 48 hours.The drug appears to be well tolerated with the most commonlyreported side effects being rash and diarrhea. It mayalso cause elevations in blood pressure especially in those patientswith preexisting hypertension, elevation of transaminaselevels, and mild nausea and mucositits.

Warnings and precautions

Gefitinib is not suitable for pregnant women, and breastfeeding women should cease breastfeeding throughout their treatment period.

Indications

Iressa (ZD1839) is an orally active tyrosine kinase inhibitor selective for the epidermal growth factor (EGF) receptor tyrosine kinase. Iressa is undergoing clinical trials in the treatment of various solid tumors, including head and neck cancer, breast cancer and non-small cell lung cancer. Its antitumor activity is derived from the fact that the EGF receptor and EGF signaling are frequently overactivated in sensitive tumors. The major side effects include diarrhea and skin rash. Bone marrow toxicity has not been a dose-limiting problem.

Brand name

Iressa (AstraZeneca).

Description

Gefitinib was introduced in Japan as a daily oral monotherapy for the treatment of inoperable or recurrent non-small cell lung cancers (NSCLC). This anilinoquinazoline derivative can be synthesized in 6 steps starting from 6,7-dimethoxyquinazolin-4(3H)-one by successive monodemethylationlacetylation of the 6-hydroxy-group followed by chlorination and reaction with 3-chloro-4-fluoroaniline, finally deacetylation and alkylation with 3-(4-morpholinyl)propylbromide complete the synthesis. Gefitinib reversibly inhibits the activity of the epidermal growth factor receptor tyrosine kinase (EGRF TK). This inhibits autophosphorylation of EGRF and blocks the cascade of intracellular events which have been implicated in the proliferation, survival and metastasis of cancer cells. Gefitinib diplays good selectivity for the EGRF TK relative to other growth factors in human umbilical endothelial cells. It is similarly selective relative to other kinases, for example cerB2. Data from two large phase II studies in patients with pretreated NSCLC have shown that gefitinib induces a response rate approaching 20% in patients receiving the agent as a second line therapy and approximately 10% in those pretreated with more lines of chemotherapy. Gefitinib has good bioavailability and is metabolized in the liver via the cytochrome P450 3A4 enzyme system with a mean elimination half life of 28 h. Gefitinib has been generally well tolerated in cancer patients with predominant side effects being acne-like skin-rash, diarrhea, nausea, vomiting and mild to moderate myelosuppression. .

Biological Activity

Orally active, selective inhibitor of EGFR tyrosine kinase (IC 50 = 23-79 nM). Shows minimal activity against ErbB2, KDR, c-flt, PKC, MEK and ERK-2. Blocks EGFR autophosphorylation and inhibits tumor growth in mice bearing a range of human xenografts.
InChI:InChI=1/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

184475-35-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (Y0001813)  Gefitinib  EuropePharmacopoeia (EP) Reference Standard 184475-35-2 Y0001813 1,880.19CNY Detail
Sigma-Aldrich (Y0001809)  Gefitinib for system suitability  EuropePharmacopoeia (EP) Reference Standard 184475-35-2 Y0001809 1,880.19CNY Detail

184475-35-2SDS

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 Gefitinib

1.2 Other means of identification

Product number -
Other names Iressa

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:184475-35-2 SDS

184475-35-2Synthetic route

3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline
199327-59-8

4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With potassium hydroxide In isopropyl alcohol at 20℃;99%
In isopropyl alcohol at 80℃; for 0.533333h; Microwave irradiation;92%
With N,N,N,N,-tetramethylethylenediamine; nickel dichloride In tetrahydrofuran at 50℃; for 0.333333h; Concentration; Temperature; Reagent/catalyst;92.5%
3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

4-iodo-7-methoxy-6-[3-(4- morpholinyl)propoxy]quinazoline

4-iodo-7-methoxy-6-[3-(4- morpholinyl)propoxy]quinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
In isopropyl alcohol Reflux;92.46%
3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

4-bromo-7-methoxy-6-[3-(4- morpholinyl)propoxy]quinazoline

4-bromo-7-methoxy-6-[3-(4- morpholinyl)propoxy]quinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
In isopropyl alcohol Reflux;92.06%
4-(3-chloropropyl)morpholine
7357-67-7

4-(3-chloropropyl)morpholine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 3h; Reagent/catalyst; Temperature;92%
With tetrabutylammomium bromide; sodium carbonate; potassium iodide In iso-butanol Reflux;90%
In N,N-dimethyl-formamide at 80 - 90℃; Concentration;88%
4-(3-((4-chloro-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine
320366-66-3

4-(3-((4-chloro-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine

1,3-dichloro-4-fluorobenzene
1435-48-9

1,3-dichloro-4-fluorobenzene

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide Reflux;91%
4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline dihydrochloride

4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline dihydrochloride

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With sodium hydroxide In water at 30 - 70℃; for 1.5h; pH=11 - 13;90.7%
3-morpholinopropyl 4-methylbenzenesulfonate
957621-67-9

3-morpholinopropyl 4-methylbenzenesulfonate

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;89.5%
2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile
675126-27-9

2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile

3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Stage #1: 2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile; N,N-dimethyl-formamide dimethyl acetal With acetic acid In toluene at 85 - 90℃; for 2h;
Stage #2: 3-chloro-4-fluorophenylamine With acetic acid In toluene at 75 - 85℃; for 2.5h; Inert atmosphere;
89.5%
methanesulfonic acid 3-morpholin-4-yl-propyl ester
1018895-28-7

methanesulfonic acid 3-morpholin-4-yl-propyl ester

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;89.2%
4-(methylthio)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline
958669-55-1

4-(methylthio)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline

3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With 3-chloro-4-fluoroaniline hydrochloride In isopropyl alcohol for 24h; Heating;85%
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With thionyl chloride; N,N-dimethyl-formamide for 1h; Reflux;
Stage #2: 3-chloro-4-fluorophenylamine In isopropyl alcohol for 1h; Reflux;
84%
With potassium carbonate In isopropyl alcohol at 80 - 85℃; for 1h;82%
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With thionyl chloride In N,N-dimethyl-formamide for 2h; Heating;
Stage #2: 3-chloro-4-fluorophenylamine In N,N-dimethyl-formamide at 100℃; for 1h; Further stages.;
73%
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With triethylamine; trichlorophosphate In toluene at 5 - 70℃;
Stage #2: 3-chloro-4-fluorophenylamine In isopropyl alcohol; toluene at 70℃; for 1h;
62.86%
Stage #1: 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one With thionyl chloride for 4h; Reflux;
Stage #2: 3-chloro-4-fluorophenylamine In i-Amyl alcohol for 6h; Reflux;
2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile
675126-27-9

2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile

N'-(3-chloro-4-fluorophenyl)-N,N-dimethylmethanimidamide

N'-(3-chloro-4-fluorophenyl)-N,N-dimethylmethanimidamide

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With acetic acid at 130℃; for 1h;84%
With acetic acid; sodium sulfate In toluene at 130℃; for 4h;70%
2-chloro-N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

2-chloro-N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; acetic acid; zinc In methanol at 0 - 45℃; for 24h;82%
morpholine
110-91-8

morpholine

6-(3-chloropropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-ylamine
912556-91-3

6-(3-chloropropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-ylamine

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide at 60℃; for 0.5h;78%
3-chloro-4-fluorophenylamine
367-21-5

3-chloro-4-fluorophenylamine

N′-[2-cyano-5-methoxy-4-{3-(4-morpholinyl)propoxy}phenyl]-N,N-dimethylformamidine

N′-[2-cyano-5-methoxy-4-{3-(4-morpholinyl)propoxy}phenyl]-N,N-dimethylformamidine

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With acetic acid at 130℃; for 3h; Temperature;78%
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 135℃;71.1%
With acetic acid at 125 - 130℃; for 3h;70%
4 (3-bromopropyl)-morpholine
125422-83-5

4 (3-bromopropyl)-morpholine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;78%
4-(3-chloropropyl)morpholine
7357-67-7

4-(3-chloropropyl)morpholine

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline
184475-71-6

4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline

A

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)-N-(3-morpholinopropyl)-quinazoline-4-amine

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)-N-(3-morpholinopropyl)-quinazoline-4-amine

B

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Stage #1: 4-(3-chloropropyl)morpholine; 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline With hydrogenchloride
Stage #2: With potassium carbonate In dimethyl sulfoxide at 80℃; for 2h; Reagent/catalyst;
A 13.5 %Chromat.
B 64.5%
C37H37ClFN4O5Pol

C37H37ClFN4O5Pol

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; not specified;44%
morpholine
110-91-8

morpholine

4-(3′-chloro-4′-fluoroanilino)-6-(3-bromopropoxy)-7-methoxyquinazoline

4-(3′-chloro-4′-fluoroanilino)-6-(3-bromopropoxy)-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
In N,N-dimethyl-formamide27%
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: P2S5 / pyridine / 24 h / Heating
2.1: aq. NaOH / methanol / 15 - 20 °C
2.2: 8.3 g / methanol; H2O / 5 h / 20 °C
3.1: 85 percent / 3-chloro-4-fluoroaniline hydrochloride / propan-2-ol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C
2: 91 percent / triethylamine / propan-2-ol / 288 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: oxalyl chloride / CHCl3; dimethylformamide / Heating
2: 70 percent / dimethylformamide / 1 h / 145 °C
View Scheme
Multi-step reaction with 3 steps
1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide; acetonitrile / 3 h / 40 - 45 °C
2: hydrogenchloride / methanol; water / 1 h / 20 °C
3: sodium hydroxide / water / 1.5 h / 30 - 70 °C / pH 11 - 13
View Scheme
7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazolin-4(3H)-thione
958669-54-0

7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazolin-4(3H)-thione

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aq. NaOH / methanol / 15 - 20 °C
1.2: 8.3 g / methanol; H2O / 5 h / 20 °C
2.1: 85 percent / 3-chloro-4-fluoroaniline hydrochloride / propan-2-ol / 24 h / Heating
View Scheme
4-(3-chloropropyl)morpholine
7357-67-7

4-(3-chloropropyl)morpholine

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 391.5 g / potassium carbonate / dimethylformamide / 3 h / 100 °C
2.1: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating
3.1: 349 g / acetic anhydride / 3 h / 110 °C
4.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
5.2: 86 percent / HCl / H2O / 90 - 130 °C
6.1: thionyl chloride / dimethylformamide / 2 h / Heating
6.2: 73 percent / dimethylformamide / 1 h / 100 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C
2.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C
3.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
4.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
5.1: formamide / 20 - 100 °C
5.2: 78 percent / 7 h / 100 °C
6.1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C
7.1: 91 percent / triethylamine / propan-2-ol / 288 h / Heating
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 4 h / 78 °C
2.1: acetic acid; sulfuric acid / 0.5 h / 0 - 40 °C
2.2: 6 h / 40 °C
3.1: sodium thiosulphite / water / 2 h / 45 °C
3.2: 0.83 h / 70 °C
4.1: sodium sulfate; acetic acid / toluene / 4 h / 130 °C
View Scheme
4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile
675126-28-0

4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
2.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
2.2: 86 percent / HCl / H2O / 90 - 130 °C
3.1: thionyl chloride / dimethylformamide / 2 h / Heating
3.2: 73 percent / dimethylformamide / 1 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C
2.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
3.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
4.1: formamide / 20 - 100 °C
4.2: 78 percent / 7 h / 100 °C
5.1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C
6.1: 91 percent / triethylamine / propan-2-ol / 288 h / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid; sulfuric acid / 0.5 h / 0 - 40 °C
1.2: 6 h / 40 °C
2.1: sodium thiosulphite / water / 2 h / 45 °C
2.2: 0.83 h / 70 °C
3.1: sodium sulfate; acetic acid / toluene / 4 h / 130 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; nitric acid / 3 h / 20 °C
2: ammonium formate; 15% palladium on carbon / ethanol / 2 h / 60 - 65 °C
3: acetic acid / 1 h / 130 °C
View Scheme
Multi-step reaction with 3 steps
1.1: nitric acid; sulfuric acid / dichloromethane / 3.5 h / 0 - 40 °C
2.1: sodium thiosulfate / water / 2 h / 48 - 53 °C
3.1: acetic acid / toluene / 2 h / 85 - 90 °C
3.2: 2.5 h / 75 - 85 °C / Inert atmosphere
View Scheme
2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile
675126-26-8

2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
1.2: 86 percent / HCl / H2O / 90 - 130 °C
2.1: thionyl chloride / dimethylformamide / 2 h / Heating
2.2: 73 percent / dimethylformamide / 1 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
2.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
3.1: formamide / 20 - 100 °C
3.2: 78 percent / 7 h / 100 °C
4.1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C
5.1: 91 percent / triethylamine / propan-2-ol / 288 h / Heating
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
isovanillin
621-59-0

isovanillin

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 391.5 g / potassium carbonate / dimethylformamide / 3 h / 100 °C
2.1: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating
3.1: 349 g / acetic anhydride / 3 h / 110 °C
4.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
5.2: 86 percent / HCl / H2O / 90 - 130 °C
6.1: thionyl chloride / dimethylformamide / 2 h / Heating
6.2: 73 percent / dimethylformamide / 1 h / 100 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 88 percent / sodium formate; formic acid; hydroxylamine sulfate / 8 h / 85 °C
2.1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C
3.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C
4.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C
5.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C
6.1: formamide / 20 - 100 °C
6.2: 78 percent / 7 h / 100 °C
7.1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C
8.1: 91 percent / triethylamine / propan-2-ol / 288 h / Heating
View Scheme
Multi-step reaction with 10 steps
1.1: aminosulfonic acid; sodium chlorite / water / 2 h / 5 - 8 °C
2.1: hydrogenchloride / 4 h / 50 - 55 °C
3.1: potassium carbonate; potassium iodide / acetone / 25 - 30 °C
3.2: Reflux
4.1: nitric acid; acetic acid / 14 h / 25 - 35 °C
5.1: acetic acid; iron / 50 - 60 °C
6.1: ethyl acetate / 12 h / Reflux
7.1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
8.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
9.1: methanesulfonic acid / chloroform / 5 h / Reflux
10.1: potassium iodide; sodium carbonate; tetrabutylammomium bromide / iso-butanol / Reflux
View Scheme
4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldoxime
934191-95-4

4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldoxime

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 349 g / acetic anhydride / 3 h / 110 °C
2.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
3.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
3.2: 86 percent / HCl / H2O / 90 - 130 °C
4.1: thionyl chloride / dimethylformamide / 2 h / Heating
4.2: 73 percent / dimethylformamide / 1 h / 100 °C
View Scheme
4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldehyde
861453-11-4

4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldehyde

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating
2.1: 349 g / acetic anhydride / 3 h / 110 °C
3.1: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C
4.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating
4.2: 86 percent / HCl / H2O / 90 - 130 °C
5.1: thionyl chloride / dimethylformamide / 2 h / Heating
5.2: 73 percent / dimethylformamide / 1 h / 100 °C
View Scheme
6-(3-chloropropoxy)-7-methoxyquinazolin-4(3H)-one
574738-93-5

6-(3-chloropropoxy)-7-methoxyquinazolin-4(3H)-one

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / SOCl2 / dimethylformamide / 4 h / Heating
2: 93 percent / propan-2-ol / 3 h / Heating
3: 78 percent / KI / dimethylformamide / 0.5 h / 60 °C
View Scheme
4-chloro-6-(3-chloropropoxy)-7-methoxyquinazoline
692059-41-9

4-chloro-6-(3-chloropropoxy)-7-methoxyquinazoline

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / propan-2-ol / 3 h / Heating
2: 78 percent / KI / dimethylformamide / 0.5 h / 60 °C
View Scheme
3-hydroxy-4-methoxybenzoate
6702-50-7

3-hydroxy-4-methoxybenzoate

gefitinib
184475-35-2

gefitinib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 95 percent / K2CO3 / dimethylformamide / 4 h / 70 °C
2: 89 percent / nitric acid; acetic acid; acetic anhydride / 6 h / 20 °C
3: 77 percent / Fe; acetic acid / methanol / 0.5 h / 50 - 60 °C
4: 92 percent / ethanol / 6 h / Heating
5: 86 percent / SOCl2 / dimethylformamide / 4 h / Heating
6: 93 percent / propan-2-ol / 3 h / Heating
7: 78 percent / KI / dimethylformamide / 0.5 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1: 76 percent / potassium carbonate / acetone / 24 h / Heating
2: 82 percent / nitric acid; trifluoroacetic acid / CH2Cl2 / 2 h / 20 °C
3: 60 percent / 1 h / 100 °C
4: hydrogen / palladium on activated carbon / methanol
5: 78 percent / 2-methoxy-ethanol / 2 h / 115 °C
6: oxalyl chloride / CHCl3; dimethylformamide / Heating
7: 70 percent / dimethylformamide / 1 h / 145 °C
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / acetone / 25 - 30 °C
1.2: Reflux
2.1: nitric acid; acetic acid / 14 h / 25 - 35 °C
3.1: acetic acid; iron / 50 - 60 °C
4.1: ethyl acetate / 12 h / Reflux
5.1: oxalyl dichloride; N-ethyl-N,N-diisopropylamine / chloroform / 12 h / 60 - 65 °C
6.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 60 - 65 °C
7.1: methanesulfonic acid / chloroform / 5 h / Reflux
8.1: potassium iodide; sodium carbonate; tetrabutylammomium bromide / iso-butanol / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 10 h / 85 °C
2.1: trimethylaluminum / hexane; dichloromethane / 5 h / 0 °C / Inert atmosphere; Reflux
3.1: trichlorophosphate / toluene / 2 h / Reflux
4.1: thionyl chloride; N,N-dimethyl-formamide / 1 h / Reflux
4.2: 1 h / Reflux
View Scheme
gefitinib
184475-35-2

gefitinib

7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-ol
199327-61-2

7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-ol

Conditions
ConditionsYield
With hydrogenchloride for 6h; Heating;98%
sodium docusate
577-11-7

sodium docusate

gefitinib
184475-35-2

gefitinib

gefitinib docusate

gefitinib docusate

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 20℃; for 3.5h;97%
propyl bromide
106-94-5

propyl bromide

gefitinib
184475-35-2

gefitinib

gefitinib-NP

gefitinib-NP

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; potassium hydroxide In tetrahydrofuran; acetonitrile at 50 - 60℃; for 24h; Inert atmosphere;95%
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

gefitinib
184475-35-2

gefitinib

C8H8O4*2C22H24ClFN4O3

C8H8O4*2C22H24ClFN4O3

Conditions
ConditionsYield
In methanol; acetonitrile at 50℃; for 4h; Temperature; Solvent;93.82%
1-bromo-butane
109-65-9

1-bromo-butane

gefitinib
184475-35-2

gefitinib

gefitinib-NB

gefitinib-NB

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; potassium hydroxide In tetrahydrofuran; acetonitrile at 50 - 60℃; for 24h; Inert atmosphere;93%
3-Carboxyphenol
99-06-9

3-Carboxyphenol

gefitinib
184475-35-2

gefitinib

C22H24ClFN4O3*C7H6O3

C22H24ClFN4O3*C7H6O3

Conditions
ConditionsYield
In methanol at 5 - 10℃; for 48.83h; Solvent;91.12%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

gefitinib
184475-35-2

gefitinib

2C22H24ClFN4O3*C10H10O4

2C22H24ClFN4O3*C10H10O4

Conditions
ConditionsYield
In ethanol at 25 - 80℃; for 17h;90%
In ethanol at 25 - 80℃;582 mg
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

gefitinib
184475-35-2

gefitinib

2C22H24ClFN4O3*C9H8O3

2C22H24ClFN4O3*C9H8O3

Conditions
ConditionsYield
In ethanol at 25 - 80℃;87.5%
In ethanol at 25 - 80℃; for 17h;87.5%
caffeic acid
331-39-5

caffeic acid

gefitinib
184475-35-2

gefitinib

2C22H24ClFN4O3*C9H8O4

2C22H24ClFN4O3*C9H8O4

Conditions
ConditionsYield
In ethanol at 25 - 80℃;83%
caffeic acid
331-39-5

caffeic acid

gefitinib
184475-35-2

gefitinib

2C22H24ClFN4O3*C9H8O4

2C22H24ClFN4O3*C9H8O4

Conditions
ConditionsYield
In ethanol at 25 - 80℃; for 18h;83%
gefitinib
184475-35-2

gefitinib

O-Demethyl-Gefitinib
847949-49-9

O-Demethyl-Gefitinib

Conditions
ConditionsYield
With pyridine hydrochloride at 170℃; for 3h;80%
With pyridine hydrochloride; potassium carbonate at 144℃; for 3h; Inert atmosphere;60.7%
With lithium chloride In N,N-dimethyl-formamide for 15h; Heating;54%
isopropyl bromide
75-26-3

isopropyl bromide

gefitinib
184475-35-2

gefitinib

gefitinib-NIP

gefitinib-NIP

Conditions
ConditionsYield
Stage #1: gefitinib With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran; water for 0.5h; Inert atmosphere;
Stage #2: isopropyl bromide In tetrahydrofuran; water at 50 - 60℃;
80%
benzoic acid
65-85-0

benzoic acid

gefitinib
184475-35-2

gefitinib

(x)C7H6O2*C22H24ClFN4O3

(x)C7H6O2*C22H24ClFN4O3

Conditions
ConditionsYield
In tetrachloromethane; acetone at 60℃; for 0.5h;69.1%

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