1401034-19-2

Basic information

• Product Name: 2-hydroxy-1-(2-((9-((1R,4R)-4-methylcyclohexyl)-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone hydrochloride
• Synonyms: 2-hydroxy-1-(2-((9-((1R,4R)-4-methylcyclohexyl)-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone hydrochloride
• CAS NO: 1401034-19-2
• Molecular Weight: 508.023
• Mol File: 1401034-19-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-hydroxy-1-(2-((9-((1R,4R)-4-methylcyclohexyl)-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-1-(2-((9-((1R,4R)-4-methylcyclohexyl)-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone hydrochloride(1401034-19-2)
• EPA Substance Registry System: 2-hydroxy-1-(2-((9-((1R,4R)-4-methylcyclohexyl)-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone hydrochloride(1401034-19-2)

Safety Data

• Hazardous Substances Data: 1401034-19-2(Hazardous Substances Data)

Upstream product

• 1401034-44-3 5-(3-fluoropyridin-4-yl)-N⁴-((1R,4R)-4-methylcyclohexyl)pyrimidine-2,4-diamine 
• 1401034-45-4 9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1401034-46-5 tert-butyl 2-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate 
• 1401034-47-6 2-(2-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-2-oxoethyl acetate 
• 1401033-86-0 2-hydroxy-1-(2-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)ethanone 
• 2523-55-9 trans-4-methylcyclohexanamine 
• 1401034-43-2 5-iodo-N⁴-((1R,4R)-4-methylcyclohexyl)pyrimidine-2,4-diamine 
• 1401034-42-1 N⁴-((1r,4r)-4-methylcyclohexyl)pyridine-2,4-diamine 
• 1151665-15-4 2-chloro-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester 
• 33483-65-7 trans-4-methylcyclohexylamine hydrochloride 
• 766545-20-4 2-chloro-5,6,7,8-tetrahydro[1,6]naphthyridine hydrochloride 
• 372-47-4 3-Fluoropyridine 

Relevant articles and documents

Multi-kilo delivery of AMG 925 featuring a buchwald-hartwig amination and processing with insoluble synthetic intermediates

The development of a synthetic route to manufacture the drug candidate AMG 925 on kilogram scale is reported herein. The hydrochloride salt of AMG 925 was prepared in 23% overall yield over eight steps from commercially available raw materials, and more than 8 kg of the target molecule were delivered. The synthetic route features a Buchwald-Hartwig amination using BrettPhos as ligand and conducted to afford 12 kg of product in a single batch. In addition, this work highlights the challenges associated with the use of poorly soluble process intermediates in the manufacture of active pharmaceutical ingredients. Creative solutions had to be devised to conduct seemingly routine activities such as salt removal, pH adjustment, and heavy metal scavenging due to the low solubility of the process intermediates. Finally, a slurry-to-slurry amidation protocol was optimized to allow for successful scale-up.