182808-04-4

Basic information

• Product Name: methyl 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate
• CAS NO: 182808-04-4
• Molecular Weight: 227.647
• Mol File: 182808-04-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 425.1±45.0 °C(Predicted)
• Density: 1.407±0.06 g/cm3(Predicted)
• CAS DataBase Reference: methyl 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate(182808-04-4)
• EPA Substance Registry System: methyl 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate(182808-04-4)

Safety Data

• Hazardous Substances Data: 182808-04-4(Hazardous Substances Data)

Usage

Uses

Methyl 4-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate is an impurity of Prucalopride (P838950), a selective 5-HT4 receptor agonist used effective for chronic constipation, but is not currently approved in the U.S. Prucalopride is approved for the treatment of chronic constipation in Europe. In addition, it is an intermediate in the preparation of enterokinetic agent R108512.

Upstream product

• 123654-26-2 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid 
• 202664-85-5 methyl 4-acetylamino-2-hydroxy-3-(2-hydroxyethyl)benzoate 
• 149466-67-1 methyl 4-acetylamino-2,3-dihydrobenzo[b]furan-7-carboxylate 
• 67-56-1 methanol 
• 143878-29-9 4-acetamido-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid methyl ester 
• 4093-31-6 methyl 2-methoxy 4-acetamido 5-chloro benzoate 

Downstream Products

• 137211-64-4 4-amino-5-chloro-2,3-dihydro-N-(4-piperidinyl)benzofuran-7-carboxamide 
• 179474-81-8 prucalopride 
• 179474-85-2 prucalopride succinate 

Relevant articles and documents

Method for preparing prucalopride intermediate

The invention belongs to the field of medicine synthesis, and particularly relates to a method for preparing a prucalopride intermediate. The method comprises the following steps: performing acylation and demethylation reactions on 2-methoxy-4-acetylamino-5-chloro methyl benzoate (I) serving as an initial raw material at 0-20 DEG C under the action of a proper amount of an acylating agent and lewis acid to obtain an intermediate (II); adding an alkaline reagent into the intermediate (II), and performing cyclization reaction at 0-20 DEG C in a polar solvent to obtain an intermediate (III); adding hydrazine hydrate and absolute ethyl alcohol to the intermediate (III), and performing reduction reaction at 70-80 DEG C to obtain an intermediate (IV); performing hydrolysis reaction on the intermediate (IV) at 90-100 DEG C under the action of a sodium hydroxide solution to obtain sodium salt of an intermediate (V), and acidizing with hydrochloric acid to obtain the intermediate (IV). The synthesizing route has mild reaction condition, low production cost and high yield, and is suitable for industrial production.

HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS

The present invention relates to novel compounds of formula (I), and their pharmaceutically acceptable salts and compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, and their pharmaceutically acceptable salts. The compounds of formula (I) are useful in the treatment of various disorders that are related to 5-HT4 receptors.

Prokinetic compounds

The present invention concerns novel oxadiazole derivatives of formula (I) STR1 the N-oxide forms, the pharmaceutically acceptable acid addition salts and the stereochemically isomeric forms thereof, wherein R1 is hydrogen or halo; R2 is C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl; R3 is hydrogen; or R2 and R3 taken together may form a C2-3 alkanediyl radical wherein one or two hydrogen atoms may be replaced by C1-4 alkyl; R4 is hydrogen or C1-6 alkyloxy; X is a bivalent radical of the formula STR2 L is a radical of formula -Alk-R5 or -Alk--O--R6, Alk is C1-12 alkanediyl; R5 is hydrogen, cyano, C1-6 alkylcarbonyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, aryl, arylcarbonyl, tetrahydrofuran, dioxolane, dioxolane substituted with C1-6 alkyl, dioxane, dioxane substituted with C1-6 alkyl; R6 is hydrogen, aryl, C1-6 alkyl, hydroxyC1-6 alkyl, C1-6 alkylcarbonyl; aryl is defined as phenyl or phenyl substituted with up to three substituents selected from halo, C1-6 alkyl or C1-6 alkyloxy. It further relates to pharmaceutical compositions comprising them, processes for preparing said compounds and compositions, and the use thereof as a medicine, in particular in the conditions involving a decreased motility of the colon.