ChemicalBook CAS DataBase List Prucalopride

Prucalopride synthesis

10synthesis methods

Product Name:Prucalopride
CAS Number:179474-81-8
Molecular formula:C18H26ClN3O3
Molecular Weight:367.87

Prucalopride is a 5-HT4R agonist. Synthetic Description Reference: Yuan, Youzhi; Tang, Jiadeng; Cen, Junda. Synthesis of Prucalopride monosuccinate. Zhongguo Yiyao Gongye Zazhi. Volume 43. Issue 1. Pages 5-8. Journal. (2012). Synthetic Description Reference: Feng, Chengliang; Yan, Bin; Zhang, Min. Preparation method of prucalopride. Assignee Jiangsu Institute of Engineering Technology, Peop. Rep. China. CN 108976216. (2018). Synthetic Description Reference: Feng, Chengliang; Yan, Bin; Zhang, Min. Preparation method of prucalopride from 3-chloro-4-methylaniline. Assignee Jiangsu Institute of Engineering Technology, Peop. Rep. China. CN 109232544. (2019). Synthetic Description Reference: Zhou, Xipeng; Pu, Yiqing; Gong, Yanchun; Lv, Fusheng; Yuan, Fang; Liu, Yongqiang. A process for preparing prucalopride succinate and its intermediates. Assignee Jiangsu Vcare Pharmatech Co., Ltd., Peop. Rep. China. CN 106146386. (2016). Synthetic Description Reference: Fu, Kaiyong; Li, Hua; Xu, Cang. Synthesis of methyl 4-acetamido-2,3-dihydrobenzofuran-7-formate. Assignee Zhiwei (Shanghai) Chemical Co., Ltd., Peop. Rep. China. CN 103012337. (2013).

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

Reference: Yuan, Youzhi; Tang, Jiadeng; Cen, Junda. Synthesis of Prucalopride monosuccinate. Zhongguo Yiyao Gongye Zazhi. Volume 43. Issue 1. Pages 5-8. Journal. (2012).

179474-79-4 Synthesis

179474-79-4
171 suppliers
$95.00/1g

123654-26-2 Synthesis

4-Amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic acid

123654-26-2
188 suppliers
$12.00/100mg

179474-81-8
210 suppliers
$11.00/5mg

Yield:179474-81-8 85%

Reaction Conditions:

Stage #1:4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid with 1,1'-carbonyldiimidazole in tetrahydrofuran for 0.416667 h;
Stage #2:4-amino-1-(3-methoxypropyl)piperidine in tetrahydrofuran at 45 - 50; for 4 h;

Steps:

8 Example 8 Synthesis of prucalopride succinic acid
THF, 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid (1.0 g), a small amount of CDI was added, stirred for 25 min,(0.8 g, GC & gt; 98%) was added dropwise to a solution of 1- (3-methoxypropyl) -4-piperidinamine (I) at 45 ° C for 4 h, (30g), precipitate a large amount of solid, stirring at 25 for 1h; pumping, 20g of water rinse, collecting filter cake, drying, diclofenac 1.5g , Yield 85% (mp = 91-92 ° C).To the reaction flask was added paclitaxel (1.0 g) and 75% ethanol (5 mL), heated to 40 ° C, and succinic acid (0.35 g) was added with stirring and stirred for 3 h. The filter cake was recrystallized from 75% ethanol and dried to give 1.17 g of white granular crystals in 93% yield

References:

Jiangsu Weikaier Pharmaceutical Technology Co., Ltd.;Zhou Xipeng;Pu Yiqing;Gong Yanchun;Lv Fusheng;Yuan Fang;Liu Yongqiang CN106146386, 2016, A Location in patent:Paragraph 0068; 0069; 0070; 0071

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