Synthetic processes and synthetic intermediates
Inventors
Ghone, Sanjeevani • Kang, Fu-An • Jain, Nareshkumar • Parhi, Ajit S. • Ponnaiah, Ravi • Soni, Anil Kumar • Athunuri, Siva Rami Reddy • Korrakuti, Thrisulapani • Seelam, Pullarao
Assignees
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Publication Number
US-10774093-B2
Publication Date
2020-09-15
Expiration Date
Abstract
The invention provides synthetic intermediates and synthetic processes that are useful for preparing the antibacterial agent TXA709:
Core Innovation
The invention provides a process for preparing the antibacterial agent TXA709 by coupling an amide of formula 9 with N-methylpiperidine-4-carboxylic acid. The coupling is carried out in a polar solvent in the presence of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride to provide TXA709.
The disclosed process further includes preparing the compound of formula 9 by reacting a compound of formula 3 with a compound of formula 8, thereby establishing a route into the amide coupling step to make TXA709. The process also includes reducing a nitro compound of formula 1 to provide a compound of formula 2.
The described sequence additionally includes preparing TXA709 mesylate, yielding a salt of formula 11. The document also references upstream intermediates and conversions used in the TXA709 route.
Claims Coverage
The document includes one independent claim directed to a process for preparing TXA709, with dependent claims refining the coupling conditions and further defining preparation of specific intermediates. The claim set centers on five inventive features.
Coupling amide of formula 9 with N-methylpiperidine-4-carboxylic acid to provide TXA709
A process for preparing TXA709 comprising coupling an amide of formula 9 with N-methylpiperidine-4-carboxylic acid in a polar solvent in the presence of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride to provide TXA709.
Coupling in dichloromethane
The polar solvent is dichloromethane.
Coupling temperature between about 0 °C and about 40 °C
Coupling is performed at a temperature between about 0 °C and about 40 °C.
Preparing compound of formula 9 by reacting compound of formula 3 with compound of formula 8
Preparing the compound of formula 9 by reacting a compound of formula 3 with a compound of formula 8.
Reducing a nitro compound of formula 1 to provide the compound of formula 2
Preparing the compound of formula 2 by reducing a nitro compound of formula 1 to provide the compound of formula 2.
Overall, claim coverage centers on forming TXA709 via coupling of an amide of formula 9 with N-methylpiperidine-4-carboxylic acid in a polar solvent using N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, with refinements that specify dichloromethane, a coupling temperature window, and defined preparation steps for key intermediates including compound of formula 9 and compound of formula 2.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Not explicitly described in patent.
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