202822-76-2

Basic information

• Product Name: Benzoic acid, 4-(acetylmethylamino)-5-chloro-2-methoxy-, methyl ester
• CAS NO: 202822-76-2
• Molecular Formula: C12H14ClNO4
• Molecular Weight: 271.7
• Mol File: 202822-76-2.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-(acetylmethylamino)-5-chloro-2-methoxy-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(acetylmethylamino)-5-chloro-2-methoxy-, methyl ester(202822-76-2)
• EPA Substance Registry System: Benzoic acid, 4-(acetylmethylamino)-5-chloro-2-methoxy-, methyl ester(202822-76-2)

Safety Data

• Hazardous Substances Data: 202822-76-2(Hazardous Substances Data)

Upstream product

• 4093-31-6 methyl 2-methoxy 4-acetamido 5-chloro benzoate 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 202822-77-3 4-(N-ethyl-N-methylamino)-5-chloro-2-methoxybenzenemethanol 
• 202822-84-2 3-[5-chloro-4-[(ethylmethylamino)-2-methoxyphenyl]-methyl]-1,3,4-oxadiazol-2-(3H)-one 
• 1007219-03-5 5-chloro-2-methoxy-4-methylamino benzoic acid sulfate 

Relevant articles and documents

3-Aminopyrrolidines from α-aminoacids: Total synthesis of (+)-nemonapride from D-alanine

(Chemical Equation Presented) The antipsychotic compound nemonapride 1 was synthesized in nine steps from D-alanine 2. The key steps for the synthesis of the 3-aminopyrrolidine moiety include a Birch reduction of a cyclic enaminoester and the reduction of a pyrrolidinone to the pyrrolidine 7. Final coupling with the benzoic acid derivative 9 gave 1 as a single enantio- and diastereomer.

3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3, 4-oxadiazol-2(3H)-one, BMS-191011: Opener of large-conductance Ca 2+-activated potassium (maxi-K) channels, identification, solubility, and SAR

Compound 8a (BMS-191011), an opener of the cloned large-conductance, Ca2+-activated potassium (maxi-K) channel, demonstrated efficacy in in vivo stroke models, which led to its nomination as a candidate for clinical evaluation. Its maxi-K channel opening properties were consistent with its structural topology, being derived by combining elements from other known maxi-K openers. However, 8a suffered from poor aqueous solubility, which complicated elucidation of SAR during in vitro evaluation. The activity of 8a in in vivo stroke models and studies directed toward improving its solubility are reported herein. Enhanced solubility was achieved by appending heterocycles to the 8a scaffold, and a notable observation was made that inclusion of a simple amino group (anilines 8k and 8l) yielded excellent in vitro maxi-K ion channel opening activity and enhanced brain-to-plasma partitioning compared to the appended heterocycles.