1401034-46-5

Basic information

• Product Name: 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
• Synonyms: 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
• CAS NO: 1401034-46-5
• Molecular Weight: 513.643
• Mol File: 1401034-46-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(1401034-46-5)
• EPA Substance Registry System: 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(1401034-46-5)

Safety Data

• Hazardous Substances Data: 1401034-46-5(Hazardous Substances Data)

Upstream product

• 1588959-28-7 C₁₆H₂₀ClN₅ 
• 1588959-18-5 C₁₁H₁₇BrN₄ 
• 1588959-12-9 C₁₁H₁₅BrClN₃ 
• 2523-55-9 trans-4-methylcyclohexanamine 
• 766545-20-4 2-chloro-5,6,7,8-tetrahydro[1,6]naphthyridine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1401034-44-3 5-(3-fluoropyridin-4-yl)-N⁴-((1R,4R)-4-methylcyclohexyl)pyrimidine-2,4-diamine 
• 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 
• 1401034-45-4 9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 33483-65-7 trans-4-methylcyclohexylamine hydrochloride 
• 372-47-4 3-Fluoropyridine 

Downstream Products

• 1401033-82-6 9-((1r,4r)-4-methylcyclohexyl)-N-(5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1401033-84-8 2-[2-({9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-y}amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]ethanol 
• 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 
• 1401034-19-2 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 
• 1401033-87-1 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-oxoacetic acid 
• 1401034-48-7 methyl 2-{[6-(2-methoxy-2-oxoacetyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]{9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl}amino}-2-oxoacetate 
• 1401033-88-2 9-[(1r,4r)-4-methylcyclohexyl]-N-[6-(3,3,3-trifluoropropyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1401033-90-6 N-[6-(2-fluoroethyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]-9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1401033-91-7 N-[6-(2-methoxyethyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl]-9-[(1r,4r)-4-methylcyclohexyl]-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine 
• 1401034-13-6 (S)-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]propan-1-one 
• 1412895-86-3 C₃₂H₄₅N₇OSi 

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.

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