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  2. 850140-72-6
Introduction
Afatinib is a potent \ irreversible dual inhibitor of epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor 2 (HER2) tyrosine kinase. This product is suitable for the treatment of the following patients: 1. Locally advanced or metastatic non-small cell lung cancer (NSCLC) with epidermal growth factor receptor (EGFR) gene sensitive mutation, No previous treatment with EGFR tyrosine kinase inhibitors (TKIs) for locally advanced or metastatic squamous histologic non-small cell lung cancer (NSCLC) during or after platinum containing chemotherapy.
Names and Identifiers
  • (S,E)-N-(4-((3-Chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
  • Afatinib E-Isomer
  • Afatinib
  • BIBW 2992
  • 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,4-a]pyrazine hydrochloride
  • BIBW-2992
  • Tovok
  • BIBW2992
  • Tomtovok
  • Afatinib (BIBW2992)
  • N-[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-Butenamide
  • C24H25ClFN5O3
  • (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
  • (2E)-N-[4-[(3-Chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-butenamide (ACI)
  • Gilotrif
  • Giotrif
  • MDL:MFCD12407405
  • InChIKey:ULXXDDBFHOBEHA-CWDCEQMOSA-N
  • Inchi:1S/C24H25ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/b4-3+/t16-/m0/s1
  • SMILES:N(C1C=CC(F)=C(Cl)C=1)C1=NC=NC2=CC(=C(C=C12)NC(=O)/C=C/CN(C)C)O[C@@H]1COCC1
Chemical and Physical Properties

Computed Properties

  • Exact Mass: 485.9g/mol
  • Surface Charge: 0
  • XLogP3: 3.6
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 8
  • Rotatable Bond Count: 8
  • Monoisotopic Mass: 485.162996g/mol
  • Monoisotopic Mass: 485.162996g/mol
  • Topological Polar Surface Area: 88.6Ų
  • Heavy Atom Count: 34
  • Complexity: 702
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1

Experimental Properties

  • LogP: 4.53590
  • PSA: 88.61000
  • Boiling Point: 676.917°C at 760 mmHg
  • Melting Point: 102°C(lit.)
  • Color/Form: Powder
  • Density: 1.380
Security Information
  • Hazard Statement:H302
  • Warning Statement:P280-P305+P351+P338
  • Storage Condition:0-10°C
  • Signal Word:Warning
Synthetic Circuit

Synthetic Circuit 1

Reaction Conditions
1.1 Reagents: Triethylamine
Reference
Graphical synthetic routes of Afatinib
Li, Qingqing; et al, Zhongguo Yiyao Gongye Zazhi, 2015, 46(4), 422-424

Synthetic Circuit 2

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Water ;  40 °C; 10 h, 40 °C
1.2 40 °C; 10 h, 40 °C
1.3 Reagents: Potassium hydroxide ,  Hydrogen ,  Lithium chloride Catalysts: Dimethylformamide ;  1 h
Reference
Synthesis and optimization of antitumor agent afatinib
Tu, Yuan-biao; et al, Huaxue Shiji, 2016, 38(8), 795-799

Synthetic Circuit 3

Reaction Conditions
1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ,  BOP reagent
1.2 -
Reference
Graphical synthetic routes of Afatinib
Li, Qingqing; et al, Zhongguo Yiyao Gongye Zazhi, 2015, 46(4), 422-424

Synthetic Circuit 4

Reaction Conditions
1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Acetonitrile ;  0 °C; 0 °C → 28 °C; 2 h, 28 °C; 28 °C → 0 °C
1.2 Solvents: Acetonitrile ,  N-Methyl-2-pyrrolidone ;  0 °C → 28 °C; 2 h, 28 °C; 28 °C → 0 °C
1.3 Reagents: Lithium hydroxide Solvents: Water ;  0 °C
Reference
Process for preparation of afatinib dimaleate and its intermediates
, India, , ,

Synthetic Circuit 5

Reaction Conditions
1.1 Solvents: Tetrahydrofuran
Reference
Graphical synthetic routes of Afatinib
Li, Qingqing; et al, Zhongguo Yiyao Gongye Zazhi, 2015, 46(4), 422-424
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