202664-83-3

Upstream product

• 91958-13-3 methyl 2-allyloxy-4-acetylaminobenzoate 
• 110751-41-2 methyl 2-hydroxy-3-allyl-4-acetaminobenzoate 
• 4093-28-1 methyl 4-acetamido-2-hydroxybenzoate 

Downstream Products

• 143878-29-9 4-acetamido-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid methyl ester 
• 149466-67-1 methyl 4-acetylamino-2,3-dihydrobenzo[b]furan-7-carboxylate 
• 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 

Relevant academic research and scientific papers

4 - (acetyl amino) - 2-hydroxy-3 - (2-oxo-ethyl) benzoic acid synthesis of methyl

The invention relates to a synthetic method of 4-(acetyl amino)-2-hydroxy-3-(2-carbonyl ethyl) methyl benzoate. The method comprises the following steps of: adding the 4-(acetyl amino)-2-hydroxy-3-(2-allyl) methyl benzoate into an ether solvent, then adding a water solution of osmium potassium, finally adding water solution of an oxidant periodate, reacting under the condition of room temperature, wherein the product is insoluble to the solvent; carrying out suction filtration to obtain the 4-(acetyl amino)-2-hydroxy-3-(2-aldehyde agent ethyl) methyl benzoate crude product; and pulping and purifying the 4-(acetyl amino)-2-hydroxy-3-(2-aldehyde agent ethyl) methyl benzoate crude product with water. In comparison with the conventional process, the process is greatly improved and has the following advantages: 1) nearly no organic or inorganic waste solvent is generated; 2) the crude product can be obtained through directly carrying out centrifuging after reaction; and 3) purification can be achieved by pulping only with a small amount of water to remove inorganic salt out of the crude product. Therefore, the process can be easily put into industrial production, and the production cost is greatly lowered by reuse of the catalyst.

Synthesis and structure-activity relationship of 3-substituted benzamide, benzo[b]furan-7-carboxamide, 2,3-dihydrobenzo[b]furan-7- carboxamide, and indole-5-carboxamide derivatives as selective serotonin 5- HT4 receptor agonists

The title compounds (6-9) were prepared and evaluated for serotonin 5- HT4 agonistic activity in in vitro tests. Introducing a propyl or allyl group at the 3-position of benzamide caused only a slight enhancement of agonistic activity. Construction of the benzo[b']furan skeleton and 2,3- dihydrobenzo[b]furan skeleton caused a significant enhancement of the activity. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2- methylbenzo[b]furan-7-carboxamide (7b) hemifumarate was as potent as cisapride. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3- dihydro-2-methylbenzo[b]furan-7-carboxamide (8a) hemifumarate, 4-amino-N-[2- (1-azabicyclo [3.3.0]octan-5-yl)ethyl]5-chloro-2,3-dihydro-2- ethylbenzo[b]furan-7-carboxamide (8c) hemifumarate, and 4-amino-N-]2-(1- azabicyclo[3.3.0]octan-5-yl]-5-chloro-2,3-dihydro-2,3-dimethylhenzo[b]furan- 7-carboxamide (8d) hemifumarate were more potent than cisapride. Furthermore, 8a hemifumarate was free from dopamine D1, D2, serotonin 5-HT1, 5-HT2 and muscarine M1, M2 receptor binding activity in the in vitro tests. On the other hand, construction of the indole skeleton caused a remarkable decrease in activity.