A building block and synthetic intermediate
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4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

Item No. 30487

Technical Information
CAS Number
183322-18-1
Molecular Formula
C14H17ClN2O4
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:4): 0.2 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
222, 244 nm
SMILES
ClC1=NC=NC2=C1C=C(OCCOC)C(OCCOC)=C2
InChi Code
InChI=1S/C14H17ClN2O4/c1-18-3-5-20-12-7-10-11(16-9-17-14(10)15)8-13(12)21-6-4-19-2/h7-9H,3-6H2,1-2H3
InChi Key
ZPJLDMNVDPGZIU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline is a building block and synthetic intermediate.1,2,3,4,5 It has been used as a precursor in the synthesis of receptor tyrosine kinase (RTK) inhibitors, dual RTK and histone deacetylase (HDAC) inhibitors, and anticancer compounds.1,2,3 It is also a synthetic intermediate in the synthesis of EGFR inhibitors, including erlotinib (Item No. 10483), with antiproliferative activity.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pandey, A., Volkots, D.L., Seroogy, J.M., et alIdentification of orally active, potent, and selective 4-piperazinylquinazolines as antagonists of the platelet-derived growth factor receptor tyrosine kinase family. J. Med. Chem. 45(17), 3772-3793 (2002).

    2. Li, W.W., Wang, X.Y., Zheng, R.L., et alDiscovery of the novel potent and selective FLT3 inhibitor 1-{5-[7-(3-morpholinopropoxy)quinazolin-4-ylthio]-[1,3,4]thiadiazol-2-yl}-3-p-tolylurea and its anti-acute myeloid leukemia (AML) activities in vitro and in vivo. J. Med. Chem. 55(8), 3852-3866 (2012).

    3. Zhang, X., Su, M., Chen, Y., et alThe design and synthesis of a new class of RTK/HDAC dual-targeted inhibitors. Molecules 18(6), 6491-6503 (2013).

    4. Liu, Z., Wang, L., Feng, M., et alNew acrylamide-substituted quinazoline derivatives with enhanced potency for the treatment of EGFR T790M-mutant non-small-cell lung cancers. Bioorg. Chem. 77, 593-599 (2018).

    5. Knesl, P., Röseling, D., and Jordis, U. Improved synthesis of substituted 6,7-dihydroxy-4-quinazolineamines: Tandutinib, erlotinib and gefitinib. Molecules 11(4), 286-297 (2006).