24036-48-4

Basic information

• Product Name: 2-chloro-N-(5-bromo-2-hydroxyphenyl)acetamide
• Synonyms: 2-chloro-N-(5-bromo-2-hydroxyphenyl)acetamide
• CAS NO: 24036-48-4
• Molecular Weight: 264.506
• Mol File: 24036-48-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-chloro-N-(5-bromo-2-hydroxyphenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-(5-bromo-2-hydroxyphenyl)acetamide(24036-48-4)
• EPA Substance Registry System: 2-chloro-N-(5-bromo-2-hydroxyphenyl)acetamide(24036-48-4)

Safety Data

• Hazardous Substances Data: 24036-48-4(Hazardous Substances Data)

Upstream product

• 107986-49-2 N-(5-bromo-2-hydroxyphenyl)acetamide 
• 614-80-2 2-(acetylamino)phenol 
• 40925-68-6 2-amino-4-bromo-phenol 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 110704-48-8 5-bromo-2-(chloromethyl)benzo[d]oxazole 
• 24036-49-5 6,7-dibromo-(2H)-1,4-benzoxazin-3(4H)-one 
• 24036-47-3 6-bromo-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 

Relevant articles and documents

Identification and development of an efficient route to SB-649915

The discovery and development of an efficient manufacturing route to the SSRI-5-HT1A receptor antagonist 6-[(1-{2-[(2-methyl-5-quinolinyl)oxy]ethyl}-4- piperidinyl)methyl]-2H-1,4-benzoxazin-3(4H)-one (SB-649915) 1 is described. The existing route to 1 involved coupling quinoline 6 with piperidine 5 and was considered lengthy as a consequence of the nine synthetic steps required to prepare 5. Two new routes to the key piperidine intermediate 5 are identified which deliver this compound in five and two steps respectively, from readily available materials using novel lithiation and Friedel-Crafts methodology respectively. The latter of these two routes was successfully demonstrated at 5 L scale to deliver 700 g of 5. Development to the methanesulfonate 34, an alternative to quinoline 6, is also described as is the final alkylation of piperidine 5 with this methanesulfonate 34 to deliver SB-649915 1.

Discovery of 4-phenyl-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives as potent and orally active PI3K/mTOR dual inhibitors

PI3K/Akt/mTOR signaling pathway plays an important role in cancer cell growth and survival. In this study, a new class of molecules with skeleton of 4-phenyl-2H-benzo[b] [1,4]oxazin-3(4H)-one were designed and synthesized targeting this pathway. Bioassays showed that, among all the molecules, 8d-1 was a pan-class I PI3K/mTOR inhibitor with an IC50 of 0.63 nM against PI3Kα. In a wide panel of protein kinases assays, no off-target interactions of 8d-1 were identified. 8d-1 was orally available, and displayed favorable pharmacokinetic parameters in mice (oral bioavailability of 24.1%). In addition, 8d-1 demonstrated significant efficiency in Hela/A549 tumor xenograft models (TGI of 87.7% at dose of 50 mg/kg in Hela model) without causing significant weight loss and toxicity during 30 days treatment. Based on the bioassays, compound 8d-1 could be used as an anti-cancer drug candidate.

THIAZOLE DERIVATIVES AS KINASE INHIBITORS

A series of thiazole derivatives which are substituted in the 2-position by a substituted morpholin-4-yl moiety, being selective inhibitors of P13 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.