1196531-35-7

Basic information

• Product Name: 2-(4-(5-cyano-2-methoxyphenoxy)piperidin-1-yl)-N-methylacetamide
• Synonyms: 2-(4-(5-cyano-2-methoxyphenoxy)piperidin-1-yl)-N-methylacetamide
• CAS NO: 1196531-35-7
• Molecular Weight: 303.361
• Mol File: 1196531-35-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(4-(5-cyano-2-methoxyphenoxy)piperidin-1-yl)-N-methylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-(5-cyano-2-methoxyphenoxy)piperidin-1-yl)-N-methylacetamide(1196531-35-7)
• EPA Substance Registry System: 2-(4-(5-cyano-2-methoxyphenoxy)piperidin-1-yl)-N-methylacetamide(1196531-35-7)

Safety Data

• Hazardous Substances Data: 1196531-35-7(Hazardous Substances Data)

Upstream product

• 141699-59-4 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate 
• 5415-94-1 2-hydroxy-N-methylacetamide 
• 1196531-36-8 4-methoxy-3-(4-piperidyloxy)benzonitrile hydrochloride 
• 1196531-33-5 tert-butyl 4-(5-cyano-2-methoxy-phenoxy)piperidine-1-carboxylate 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 96-30-0 chloroacetylmethylamide 

Downstream Products

• 1196531-37-9 2-[4-(5-cyano-2-methoxy-4-nitro-phenoxy)-1-piperidyl]-N-methylacetamide 
• 848942-61-0 Sapitinib 

Relevant articles and documents

The Development of a Dimroth Rearrangement Route to AZD8931

Recently, the aminoquinazoline motif has been highly prevalent in anticancer pharmaceutical compounds. Synthetic methods are required to make this structure on a multikilo scale and in high purity. The initial route to aminoquinazoline AZD8931 suffered from the formation of late-stage impurities. To avoid these impurities, a new high-yielding Dimroth rearrangement approach to the aminoquinazoline core of AZD8931 was developed. Assessment of route options on a gram scale demonstrated that the Dimroth rearrangement is a viable approach. The processes were then evolved for large-scale production with learning from a kilo campaign and two plant-scale manufactures. Identification of key process impurities offers an insight into the mechanisms of the Dimroth rearrangement as well as the hydrogenation of a key intermediate. The final processes were operated on a 30 kg scale delivering the target AZD8931 in 41% overall yield.

PROCESS 738

Processes for the preparation of 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[1-(N- methylcarbamoylmethyl)piperidin-4-yl]oxy}quinazoline, salts thereof, and the intermediates used in the process are described.