(S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate

Base Information

• Chemical Name: (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate
• CAS No.: 618061-76-0
• Molecular Formula: C24H27ClFN4O6P
• Molecular Weight: 552.927
• European Community (EC) Number: 808-286-6
• UNII: D8XUT95J9B
• DSSTox Substance ID: DTXSID70575639
• Wikidata: Q72451142
• Mol file: 618061-76-0.mol

Synonyms:618061-76-0;(S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate;CID 15606393;Diethyl (S)-(2-((4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)amino)-2-oxoethyl)phosphonate;N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-2-diethoxyphosphorylacetamide;P-[2-[[4-[(3-CHLORO-4-FLUOROPHENYL)AMINO]-7-[[(3S)-TETRAHYDRO-3-FURANYL]OXY]-6-QUINAZOLINYL]AMINO]-2-OXOETHYL]PHOSPHONIC ACID DIETHYL ESTER;C24H27ClFN4O6P;D8XUT95J9B;SCHEMBL436188;DTXSID70575639;FNGRCLBEXKFSST-INIZCTEOSA-N;AMY40129;MFCD19440885;AKOS025405463;AS-75229;diethyl [({4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-oxolan-3-yloxy]quinazolin-6-yl}carbamoyl)methyl]phosphonate;Diethyl {[4-(3-Chloro-4-Fluoro-Phenylamino)-7-((S)-Tetrahydrofuran-3-Yloxy)-Quinazolin-6-Ylcarbamoyl]-Methyl}-Phosphonate;Diethyl-{[4-((3-chloro-4-fluorophenyl)amino)-7-(((S)-tetrahydro-furan-3-yloxy)quinazolin-6-yl)carbamoyl]methyl}phosphonate;PHOSPHONIC ACID,[2-[[4-[(3-CHLORO-4-FLUOROPHENYL)AMINO]-7-[[(3S)-TETRAHYDRO-3-FURANYL]OXY]-6-QUINAZOLINYL]AMINO]-2-OXOETHYL]-, DIETHYL ESTER;CS-0008486;NS00077605;C75900;A918524;Diethyl (S)-2-Amino-2-oxoethyl Phosphonate Afatinib;(S)-Diethyl (2-((4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)amino)-2-oxoethyl)phosphonate;(S)-diethyl2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate;Diethyl (2-{[4-(3-chloro-4-fluoroanilino)-7-{[(3S)-oxolan-3-yl]oxy}quinazolin-6-yl]amino}-2-oxoethyl)phosphonate;Diethyl P-[2-[[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]amino]-2-oxoethyl]phosphonate;Phosphonic acid, [2-[[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]amino]-2-oxoethyl]-, diethyl ester;Phosphonic acid, P-[2-[[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]amino]-2-oxoethyl]-, diethyl ester

Chemical Property of (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate

Chemical Property:

• Boiling Point: 709.948 °C at 760 mmHg
• Flash Point: 383.163 °C
• PSA: 130.71000
• Density: 1.425 g/cm³
• LogP: 5.68420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 552.1340774
• Heavy Atom Count: 37
• Complexity: 792

Purity/Quality:

99.0%, High purity. ^*data from raw suppliers

(S)-Diethyl2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(CC(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)OC4CCOC4)OCC
• Isomeric SMILES: CCOP(=O)(CC(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)O[C@H]4CCOC4)OCC
• Uses: Diethyl (S)-2-Amino-2-oxoethyl Phosphonate Afatinib is an impurity of Afatinib (A355300), which is an aminocrotonylamino-substituted quinazoline derivative used for treating cancer and diseases of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder.

Technology Process of (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate

There total 6 articles about (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline (314771-76-1,402855-03-2) + diethylphosphonoacetic acid (3095-95-2) → (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate (618061-76-0)

Guidance literature:

diethylphosphonoacetic acid; With 1,1'-carbonyldiimidazole; at 20 ℃;

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 4 - 5h;

Reference yield: 88.0%

diethylphosphonoacetic acid (3095-95-2) + 4-[(3-chloro-4-fluoro-phenyl)amino]-6-amino-[(S)-(tetrahydrofuran-3-yl)oxy]-quinazoline → (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate (618061-76-0)

Guidance literature:

With 1,1'-carbonyldiimidazole; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 4 - 5h;

Reference yield: 69.8%

N4-(3-chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy) quinazoline-4,6-diamine (314771-76-1,402855-03-2) → (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate (618061-76-0)

Guidance literature:

diethylphosphonoacetic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 40 ℃; for 0.5h;

N₄-(3-chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy) quinazoline-4,6-diamine; In tetrahydrofuran; at 30 - 40 ℃; for 2h;

upstream raw materials:

diethylphosphonoacetic acid

N₄-(3-chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy) quinazoline-4,6-diamine

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

Downstream raw materials:

4-[(3-chloro-4-fluorophenyl)amino]-6-{[4-(homomorpholin-4-yl)-1-oxo-2-buten-1-yl]amino}-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

afatinib

4-[(3-chloro-4-fluorophenyl)amino]-6-{[4-(N,N-dimethylamino)-1-oxo-2-buten-1-yl]amino}-7-((R)-tetrahydrofuran-3-yloxy)-quinazoline

(S,E)-N-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide dimaletate

Refernces

• 1、 -. "CRYSTALLINE FORMS OF AFATINIB DI-MALEATE". Paragraph 0095. . Retrieved 2015/07/16.
• 2、 -. "Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them". Page/Page column 5. . Retrieved 2008/06/13.