179474-85-2 Usage
Chemical Properties
Butanedioic acid 4-amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide is Off-White to Pale Brown Solid
Uses
Different sources of media describe the Uses of 179474-85-2 differently. You can refer to the following data:
1. Butanedioic acid 4-amino-5-chloro-2,3-dihydro-N-[1-(3-methoxypropyl)-4-piperidinyl]-7-benzofurancarboxamide is 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.
2. Prucalopride is 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.
Clinical Use
Prucalopride succinate, a first-in-class dihydrobenzofurancarboxamide, is a selective serotonin (5-
HT4) receptor agonist. The drug, marketed under the brand name Resolor?, possesses
enterokinetic activity and was developed by the Belgian-based pharmaceutical firm Movetis.
Prucalopride alters colonic motility patterns via serotonin 5-HT4 receptor stimulation, triggering the
central propulsive force for defecation.
Synthesis
The preparation of prucalopride succinate begins with
the commercially available salicylic aniline 124. Acidic esterification, acetylation of the
aniline nitrogen atom, and ambient-temperature chlorination via sulfuryl chloride (SO2Cl2) converted
aminophenol 124 to acetamidoester 125 in 83% yield over the course of three steps. An
unique set of conditions involving sodium tosylchloramide (chloramine T) trihydrate and sodium iodide were then employed to convert 125 to o-phenolic iodide 126, which then underwent sequential
Sonogashira/cyclization reaction utilizing TMS-acetylene with tetramethylguanidine (TMG) in the
presence of silica gel to furnish the benzofuran progenitor of 127. Hydrogenation of this
intermediate benzofuranyl Sonagashira product saturated the 2,3-benzofuranyl bond while leaving the
chlorine atom intact, ultimately delivering dihydrobenzofuran 127 in excellent yield for the two step
sequence. Base-induced saponification and acetamide removal gave rise to acid 128. This acid was
activated as the corresponding mixed anhydride and treated with commercial piperidine 129 to construct
prucalopride which was stirred at room temperature for 24 hours in ethanolic succinic acid to provide
prucalopride succinate (XI). The yield for the formation of the salt was not provided.
Check Digit Verification of cas no
The CAS Registry Mumber 179474-85-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,9,4,7 and 4 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 179474-85:
(8*1)+(7*7)+(6*9)+(5*4)+(4*7)+(3*4)+(2*8)+(1*5)=192
192 % 10 = 2
So 179474-85-2 is a valid CAS Registry Number.
179474-85-2Relevant articles and documents
Continuous synthesis method of succinate (by machine translation)
-
, (2020/09/16)
The invention discloses a method for continuously synthesizing succinic acid, which is designed according to 3D printing technology, and sequentially combines the chlorination, hydrolysis, condensation, salt forming and refining steps of 4 -acetylamino -2, 3 -dihydrobenzofuran -7 - methyl formate into each reaction chamber to realize the continuous synthesis of drugs. To the method, tedious manual operation is not needed, chemical synthesis is carried out rapidly, the yield of a synthetic route is improved in a flowing chemical manner, and the safety problem caused by manual operation is avoided. The method provided by the invention can greatly reduce the cost generated in the aspects of drug storage, transportation and the like, thereby improving the medicine supply efficiency and stability, and bringing great economic and social benefits for the development of the pharmaceutical industry. (by machine translation)
A process for the preparation of intermediate the Pu card must benefit new process (by machine translation)
-
, (2017/07/20)
The invention discloses a compound of formula (I) indicated by the 1 - (3 - a oxygen propyl) - 4 - amino piperdine preparation method, it includes such as the following steps: (1) a compound of formula (II) in the reaction in a solution of ammonia the system results in the type (III) compound; (2) the compound of formula (III) with 1, 3 - dibromo - 5, 5 - dimethyl hydantoin in the reaction under alkaline condition is the system results in the type (I) compound. This preparation method without special reaction equipment requirements, the operation is simple, and is suitable for industrial production; high yield, three wastes, low cost; high purity, heavy metal residue problem. (by machine translation)
