Gefitinib supplier | CasNO.184475-35-2

Name
Gefitinib
EINECS 643-034-7
CAS No. 184475-35-2
Article Data53
CAS DataBase
Density 1.322 g/cm³
Solubility
Melting Point 119-120 °C
Formula C₂₂H₂₄ClFN₄O₃
Boiling Point 586.8 °C at 760 mmHg
Molecular Weight 446.909
Flash Point 308.7 °C
Transport Information
Appearance light-yellow crystalline powder
Safety 24/25
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms N-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine;ZD1839;4-(3-Chloro-4-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline;Irressat;Gefitinib (JAN/USAN);4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-;ZD 1839;4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-;
PSA 68.74000
LogP 4.28650

Synthetic route

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

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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%

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

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
In isopropyl alcohol Reflux;	92.46%

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

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
In isopropyl alcohol Reflux;	92.06%

: 7357-67-7
4-(3-chloropropyl)morpholine

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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%

: 320366-66-3
4-(3-((4-chloro-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide Reflux;	91%

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With sodium hydroxide In water at 30 - 70℃; for 1.5h; pH=11 - 13;	90.7%

: 957621-67-9
3-morpholinopropyl 4-methylbenzenesulfonate

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;	89.5%

: 675126-27-9
2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile

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

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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%

...Expand

: 1018895-28-7
methanesulfonic acid 3-morpholin-4-yl-propyl ester

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Solvent; Temperature;	89.2%

: 958669-55-1
4-(methylthio)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With 3-chloro-4-fluoroaniline hydrochloride In isopropyl alcohol for 24h; Heating;	85%

: 199327-61-2
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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;

: 675126-27-9
2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; acetic acid; zinc In methanol at 0 - 45℃; for 24h;	82%

: 110-91-8
morpholine

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With potassium iodide In N,N-dimethyl-formamide at 60℃; for 0.5h;	78%

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

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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%

: 125422-83-5
4 (3-bromopropyl)-morpholine

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;	78%

: 7357-67-7
4-(3-chloropropyl)morpholine

: 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

B: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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%

...Expand

: C37H37ClFN4O5Pol

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; not specified;	44%

: 110-91-8
morpholine

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

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	27%

: 199327-61-2
7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 958669-54-0
7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazolin-4(3H)-thione

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 7357-67-7
4-(3-chloropropyl)morpholine

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 675126-28-0
4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 675126-26-8
2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 621-59-0
isovanillin

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 934191-95-4
4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldoxime

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 861453-11-4
4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldehyde

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

Yield

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

: 574738-93-5
6-(3-chloropropoxy)-7-methoxyquinazolin-4(3H)-one

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 692059-41-9
4-chloro-6-(3-chloropropoxy)-7-methoxyquinazoline

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 6702-50-7
3-hydroxy-4-methoxybenzoate

: 184475-35-2
gefitinib

Conditions

Conditions	Yield
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

: 184475-35-2
gefitinib

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

Conditions

Conditions	Yield
With hydrogenchloride for 6h; Heating;	98%

: 577-11-7
sodium docusate

: 184475-35-2
gefitinib

: gefitinib docusate

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 3.5h;	97%

: 106-94-5
propyl bromide

: 184475-35-2
gefitinib

: gefitinib-NP

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; potassium hydroxide In tetrahydrofuran; acetonitrile at 50 - 60℃; for 24h; Inert atmosphere;	95%

: 121-34-6
3-methoxy-4-hydroxybenzoic acid

: 184475-35-2
gefitinib

: C8H8O4*2C22H24ClFN4O3

Conditions

Conditions	Yield
In methanol; acetonitrile at 50℃; for 4h; Temperature; Solvent;	93.82%

: 109-65-9
1-bromo-butane

: 184475-35-2
gefitinib

: gefitinib-NB

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; potassium hydroxide In tetrahydrofuran; acetonitrile at 50 - 60℃; for 24h; Inert atmosphere;	93%

: 99-06-9
3-Carboxyphenol

: 184475-35-2
gefitinib

: C22H24ClFN4O3*C7H6O3

Conditions

Conditions	Yield
In methanol at 5 - 10℃; for 48.83h; Solvent;	91.12%

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 184475-35-2
gefitinib

: 2C22H24ClFN4O3*C10H10O4

Conditions

Conditions	Yield
In ethanol at 25 - 80℃; for 17h;	90%
In ethanol at 25 - 80℃;	582 mg

: 7400-08-0
p-Coumaric Acid

: 184475-35-2
gefitinib

: 2C22H24ClFN4O3*C9H8O3

Conditions

Conditions	Yield
In ethanol at 25 - 80℃;	87.5%
In ethanol at 25 - 80℃; for 17h;	87.5%

: 331-39-5
caffeic acid

: 184475-35-2
gefitinib

: 2C22H24ClFN4O3*C9H8O4

Conditions

Conditions	Yield
In ethanol at 25 - 80℃;	83%

: 331-39-5
caffeic acid

: 184475-35-2
gefitinib

: 2C22H24ClFN4O3*C9H8O4

Conditions

Conditions	Yield
In ethanol at 25 - 80℃; for 18h;	83%

: 184475-35-2
gefitinib

: 847949-49-9
O-Demethyl-Gefitinib

Conditions

Conditions	Yield
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%

: 75-26-3
isopropyl bromide

: 184475-35-2
gefitinib

: gefitinib-NIP

Conditions

Conditions	Yield
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%

: 65-85-0
benzoic acid

: 184475-35-2
gefitinib

: (x)C7H6O2*C22H24ClFN4O3

Conditions

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

Gefitinib Specification

1. Introduction of Gefitinib

Gefitinib is an light-yellow crystalline Powder. With the IUPAC Name of N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy) quinazolin-4-amine, it belongs to the Product Categories which include Active Pharmaceutical Ingredients; Gefitinib; Molecular Targeted Antineoplastic; Intermediates & Fine Chemicals; Pharmaceuticals; Pharmaceutical intermediate. Gefitinib is a drug used in the treatment of certain types of cancer.

2. Properties of Gefitinib

Gefitinib has the following datas: (1)Molar Volume: 337.7 cm³; (2)Polarizability: 47.09×10-24cm³; (3)Surface Tension: 55.2 dyne/cm; (4)Density: 1.322 g/cm³; (5)Flash Point: 308.7 °C; (6)Enthalpy of Vaporization: 87.63 kJ/mol; (7)Melting Point: 119-120 °C; (8)Boiling Point: 586.8 °C at 760 mmHg; (9)Vapour Pressure: 9.48E-14 mmHg at 25°C.

3. Structure Descriptors of Gefitinib

You could convert the following datas into the molecular structure:
(1).Canonical SMILES: COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
(2).InChI: InChI=1S/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)
(3).InChIKey: XGALLCVXEZPNRQ-UHFFFAOYSA-N

Product Name

Gefitinib

Synthetic route

Gefitinib Specification

Related Products

Hot Products