926319-53-1

Basic information

• Product Name: 6-(benzyloxy)-8-(2-broMoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one
• Synonyms: 6-(benzyloxy)-8-(2-broMoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one;2H-1,4-Benzoxazin-3(4H)-one, 8-(2-broMoacetyl)-6-(phenylMethoxy)-;8-(Bromoacetyl)-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one
• CAS NO: 926319-53-1
• Molecular Formula: C₁₇H₁₄BrNO₄
• Molecular Weight: 376.20136
• Mol File: 926319-53-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 552.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.509±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DCM, Methanol
• PKA: 11.70±0.20(Predicted)
• CAS DataBase Reference: 6-(benzyloxy)-8-(2-broMoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(benzyloxy)-8-(2-broMoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one(926319-53-1)
• EPA Substance Registry System: 6-(benzyloxy)-8-(2-broMoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one(926319-53-1)

Safety Data

• Hazardous Substances Data: 926319-53-1(Hazardous Substances Data)

Usage

Uses

8-(Bromoacetyl)-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one is an intermediate in the synthesis of Olodaterol (O262000), a novel inhaled β2-adrenoceptor agonist with a 24h bronchodilatory efficacy.

InChI:InChI=1S/C17H14BrNO4/c18-8-15(20)13-6-12(22-9-11-4-2-1-3-5-11)7-14-17(13)23-10-16(21)19-14/h1-7H,8-10H2,(H,19,21)

Upstream product

• 100-39-0 benzyl bromide 
• 861841-90-9 1-[2-hydroxy-3-amino-5-(benzyloxy)phenyl]ethanone 
• 861841-94-3 1‐[2-hydroxy-3-nitro-5-(benzyloxy)phenyl]ethanone 
• 30992-63-3 5-benzyloxy-2-hydroxyacetophenone 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 100-44-7 benzyl chloride 
• 131341-58-7 2,5'-dihydroxy acetophenone 
• 123-31-9 hydroquinone 
• 1205-91-0 benzene-1,4-diyl diacetate 
• 869478-09-1 8-acetyl-6-(phenylmethoxy)-4H-1,4-benzoxazin-3-one 

Downstream Products

• 869477-96-3 Olodaterol hydrochloride 
• 926319-48-4 6-(phenylmethoxy)-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one hydrochloride 
• 869478-12-6 8-(2R)-oxirane-6-(phenylmethoxy)-2H-1,4-benzoxazine-3(4H)-one 

Relevant articles and documents

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists

A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.

Benzoxazine compound and its preparation methods and application

The invention relates to a benzoxazine compound represented in the following formula 1. The benzoxazine compound can serve as a beta 2 receptor agonist. The formula can be seen from the description.

PROCESS FOR THE MANUFACTURING OF BETA MIMETICS

The invention relates to a method for producing betamimetics of formula (1), wherein in which n represents 1 or 2; R1 represents hydrogen, halogen, C1-4-alkyl or O—C1-4-alkyl; R2 represents hydrogen, halogen, C