Synthesis of Gefitinib

Abstract
References
Similar articles

Download: PDF (0 KB) HTML (1 KB) Export: BibTeX | EndNote (RIS) Supporting Info

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％.

	Service

	E-mail this article gefitinib\|tyrosine kinase inhibitor\|Fe-Al-Cu complex catalyst\|synthesis ”. Please open it by linking:" name=neirong>
	Add to my bookshelf
	Add to citation manager
	E-mail Alert
	RSS
	Articles by authors

Key words： font-family: "TimesNewRomanPSMT","serif" mso-hansi-font-family: Calibri mso-hansi-theme-font: minor-latin mso-bidi-font-family: TimesNewRomanPSMT mso-font-kerning: 0pt mso-ansi-language: EN-US mso-fareast-language: ZH-CN gefitinib')" href="#">mso-bidi-language: AR-SA">gefitinib tyrosine kinase inhibitor Fe-Al-Cu complex catalyst synthesis

Cite this article:

. 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.

[1]	LIU Changchun, ZHOU Xinxin, MIN Qin, HOU Yueyang, CHEN Qiuyun. Improved Synthesis of Dacomitinib[J]. CJPH, 2021, 52(11): 1464-1467.
[2]	HUANG Lu, GU Shuangxi, HONG Yi. Overview on Highly Selective Rearranged during Transfection Tyrosine Kinase Inhibitors and Their Patents[J]. CJPH, 2021, 52(10): 1291-1296.
[3]	ZHANG Lijuan1, HAN Xiao1, CHEN Rui2, CHEN Huiqiong3. Improved Synthesis of Cabozantinib (S)-Malate*[J]. CJPH, 2019, 50(03): 284-286.
[4]	TANG Jianqiu1,2, TANG Song2, ZHU Yizhong2, CHEN Guoguang1, REN Lili1TANG Jianqiu1,2, TANG Song2, ZHU Yizhong2, CHEN Guoguang1, REN Lili1. Synthesis of Lenvatinib[J]. CJPH, 2018, 49(06): 753-.
[5]	DENG Qishan, SHI Qing, ZHENG Zhebin. Synthesis of Ponatinib*[J]. CJPH, 2014, 45(9): 812-815.
[6]	XIE Ning1,2, LI Yanyang1, SUN Huifang1,3, ZHAO Yanjin1, LI Shuxin1,2. Synthesis of Cabozantinib (S)-Malate*[J]. CJPH, 2014, 45(3): 207-210.
[7]	FANG Zheng1, MA Xiangjun2, XU Jiafeng2, WEI Ping2, GUO Kai2. Synthesis of Axitinib*[J]. CJPH, 2014, 45(12): 1104-1107.
[8]	GUO Jialin1,2, YANG Yihong1, XIAO Junhai2. Synthesis of Imatinib Mesylate*[J]. CJPH, 2013, 44(7): 644-647.
[9]	ZHOU Feng, ZHENG Canhui, ZHU Ju, LIU Jia, ZHOU Youjun. Synthsis of Substituted 1,3-Dihydroindolin-2-ones*[J]. CJPH, 2013, 44(7): 660-662.
[10]	CAI Ji-Lan, YANG Zhan-Xiong, DU You-Guo, LIU Wen-Jie. Synthesis of Pelitinib[J]. CJPH, 2013, 44(2): 125-127.
[11]	CHEN Hong, WANG Yingli, LIU Tongbin. Synthesis of Bosutinib*[J]. CJPH, 2013, 44(11): 1086-1088.
[12]	LI Shi-Hang1, YE Rui-Fang1, 吕He-Ping2 , MAO Quan-Gui2, DAI Wei2. Optimization of Fermentation Medium of Demethylchlortetracycline and Mechanism Analysis*[J]. CJPH, 2012, 43(11): 896-902.
[13]	CHEN Shuang-Xi1, ZHANG Le-Le1, ZHU Li-Juan1, HUANG Wei-Min2. Effect of Taylor Vortex Column on Inosine Fermentation Process[J]. CJPH, 2012, 43(11): 902-904.