gefitinib,tyrosine kinase inhibitor,Fe-Al-Cu complex catalyst,synthesis," /> Synthesis of Gefitinib
中国医药工业杂志
 
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CJPH  2013, Vol. 44 Issue (11): 1081-1083    DOI:
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Synthesis of Gefitinib
1. School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222001; 2. Lianyungang Shenghe Biotechnology Limited Company, Lianyungang 222007
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Abstract Gefitinib was synthesized from 3-hydroxy-4-methoxybenzaldehyde via conversion of aldehyde to nitrile, condensation with N-(3-chloropropy1)morpholine, nitration and reduction to give 2-amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)benzonitrile, which was subjected to amidination with 3-chloro-4-fluoroaniline and cyclization in the presence of formic acid with an overall yield of about 44%.
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. Synthesis of Gefitinib[J]. CJPH, 2013, 44(11): 1081-1083.
 
[1] Fry DW, Kraker AJ, McMichael A, et al. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase [J]. Science, 1994, 265(5175): 1093-1095.
[2] Barker AJ, Gibson KH, Grundy W, et al. Studies leading to the identification of ZD1839 (IRESSA): an orally active, selective epidermal growth factor receptor tyrosine kinase
[3] inhibitor targeted to the treatment of cancer [J]. Bioorg Med Chem Lett, 2001, 11(14): 1911-1914.
[4] 张艳华, 宁 华, 姜 洋. 表皮生长因子受体酪氨酸激酶抑制剂吉非替尼[J]. 中国新药杂志, 2004, 13(10): 947-950.
[5] Gibson KH. Preparation of haloanilinoquinazolines as Class I receptor tyrosine kinase inhibitors: WO, 9633980 [P]. 1996-10-31.
[6] Gilday JP, Moody D. Process for the preparation of 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy) quinazoline: WO, 2004024703 [P]. 2004-03-25.
[7] Wang JQ, Gao MZ, Miller KD, et al. Synthesis of [11C] Iressa as a new potential PET cancer imaging agent for epidermal growth factor receptor tyrosine kinase [J]. Bioorg Med Chem Lett, 2006, 16(15): 4102-4106.
[8] 刁圆圆, 张庆文. 吉非替尼的合成[J]. 中国医药工业杂志, 2008, 39(6): 401-403.
[9] Ramanadham JP, Muddasani PR, Bollepalli NR, et al. An improved process for the preparation of gefitinib: WO, 2005070909 [P]. 2005-08-04.
[10] 李美松, 尚海萍. 吉非替尼合成路线图解[J]. 中国医药工业杂志, 2011, 42(10): 796-798.
[11] 陈 宇, 竺 伟, 陈欢生. 吉非替尼的合成[J]. 中国医药工业杂志, 2013, 44(5): 428-430. 浏览
[12] George AO, Takashi K. Synthetic methods and reactions. 601. Improved one-step conversion of aldehydes into nitrileswith hydroxylamine in formic acid solution [J]. Synth Commun, 1979, 232: 112-113.
[13] 张竹霞, 吕荣文, 张珂珂, 等. 水合肼还原芳硝基物的研究[J]. 精细化工, 2001, 18(4): 239-242.
[14] Rousselet G, Capdevielle P, Maumy M. Copper(I)-induced addition of amines to unactivated nitriles: The first general one-step synthesis of alkyl amidines [J]. Tetrahedron Lett, 1993, 34(40): 6395-6398.
[15] MurtyM SR, Jyothirmai B, Krishna PR, et al. Zinc mediated alkylation of cyclic secondary amines [J]. Synth Commun, 2003, 33(14): 2483-2486.
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