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- Title
Synthesis and Spectral Characterization of 4,7-Dichloro-6-nitroquinazoline.
- Authors
Nguyen, Thi Ngoc; Tran, Thi Huong; Dao, Nguyet Suong Huyen; Nguyen, Van Giang; Nguyen, Dinh Luyen; Trinh, Nguyen Trieu; Nguyen, Van Hai
- Abstract
Afatinib is a 4-anilinoquinazoline tyrosine kinase inhibitor (TKI) in the form of a dimaleate salt which is indicated for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC). The most scalable route for the synthesis of this drug was reported in two Boehringer Ingelheim patents, in which the title compound, 4,7-dichloro-6-nitroquinazoline (IV), is an important intermediate. Compound IV is also present in a number of synthetic pathways for various 4,7-disubstituted quinazoline derivatives displaying high therapeutic potential. However, no detailed characterization of this popular compound has been reported, possibly due to its high instability. In this paper, IV was prepared in an overall yield of 56.1% by a 3-step process (condensation, nitration, and chlorination) from 2-amino-4-chlorobenzoic acid (I). The target compound has been for the first time fully characterized by melting point, mass-spectrometry, FT-IR, 1H-NMR and 13C-NMR spectroscopies.
- Subjects
BOEHRINGER Ingelheim Pharmaceuticals Inc.; NON-small-cell lung carcinoma; MELTING points; DRUG synthesis; PROTEIN-tyrosine kinases
- Publication
Molbank, 2020, Vol 2020, Issue 2, pM1134
- ISSN
1422-8599
- Publication type
Academic Journal
- DOI
10.3390/M1134