ChemicalBook CAS DataBase List Savolitinib

Savolitinib synthesis

7synthesis methods

Product Name:Savolitinib
CAS Number:1313725-88-0
Molecular formula:C17H15N9
Molecular Weight:345.36

The synthesis of savolitinib started with 6-amino-3-carboxypyridine (20.1), which was treated with chloroacetaldehyde to generate the imidazopyridine 20.2. The carboxylic acid was converted to the Weinreb amide 20.3 and treated with methylmagnesium bromide to give the methyl ketone 20.4. The ketone was converted to the chiral amine 20.5 using a commercially available aminotransferase with the cofactors pyridoxal phosphate and isopropylamine as a nitrogen source. After process workup, the amine was isolated as the dihydrochloride salt (20.5). The free base was obtained by treatment with alkaline conditions, which was subsequently reacted with commercially available 3,5-dibromopyrazin-2-amine (20.6) to give the secondary amine 20.7. Next, nitrosyl ion formation and cyclization gave the 1,2,3-triazole 20.8. Finally, Suzuki coupling with 20.9 completed the construction of savolitinib (20). The boronic acid ester 20.9 was obtained from 4-bromo-1-methyl-1H-pyrazole by lithium-halogen exchange and workup with triisopropylborate quenching.

3167-49-5 Synthesis

3167-49-5
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1313725-88-0
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Yield:-

Steps:

Multi-step reaction with 8 steps
1.1: water / 4 h / 75 - 80 °C / Large scale
2.1: 1,1'-carbonyldiimidazole / acetonitrile / 16 h / 10 - 20 °C / Large scale
2.2: 24 h / 5 - 12 °C / Large scale
3.1: tetrahydrofuran / 8 h / 5 - 20 °C / Large scale
4.1: isopropylamine hydrochloride; sodium tetraborate decahydrate; amine transaminase-436; pyridoxal 5'-phosphate; sodium hydroxide / water; dimethyl sulfoxide / 72 h / 44 - 54 °C / pH 10 / Enzymatic reaction
5.1: ammonia / water; dichloromethane / 10 - 20 °C
6.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 120 °C
7.1: sodium nitrite; acetic acid / water / 4 h / 5 °C
7.2: 4 h / 25 °C
8.1: potassium carbonate / water; iso-butanol / 0.08 h / Inert atmosphere
8.2: 2 h / 30 - 65 °C / Inert atmosphere

References:

ASTRAZENECA AB;HUTCHISON MEDIPHARMA LIMITED;TURNER, Andrew, Roy;TURNER, Andrew, Timothy;HOWELL, Gareth, Paul;GALL, Malcolm, Allan, Young;MULHOLLAND, Keith, Raymond;ADLINGTON, Neil, Keith;TIAN, Zhenping;LIU, Bo;GONG, Qisun;YU, Wei WO2020/53198, 2020, A1

1313723-58-8
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1313725-89-1
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1313725-88-0
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References

N-methoxy-N-methylimidazo[1,2-a]pyridine-6-carboxamide

1313726-20-3
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1313725-88-0
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References

139022-25-6 Synthesis

imidazo[1,2-a]pyridine-6-carboxylic acid

139022-25-6
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1313725-88-0
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References

1270475-03-0 Synthesis

alpha-Methylimidazo[1,2-a]pyridine-6-methanamine

1270475-03-0
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1313725-89-1
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1313725-88-0
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References

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Savolitinib synthesis

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