Amino acid compounds and methods of use
A compound, aminopyridine technology, applied in the field of therapeutic agents, can solve problems such as few treatment options
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Synthetic example
[0745] The chemical reactions in the synthetic examples described can be readily adapted to prepare many other compounds of the invention, and alternative methods for preparing compounds of the invention are considered to be within the scope of the invention. For example, by modifications apparent to those skilled in the art (e.g. by suitably protecting interfering groups), by utilizing other suitable reagents known in the art than those described or by routine modification of the reaction conditions, Synthesis of non-exemplary compounds according to the invention can be successfully performed. Alternatively, other reactions disclosed herein or known in the art will be considered to have applicability for the preparation of other compounds of the invention. In the following examples, certain compounds are labeled as racemates, separated isomers, or have unassigned absolute stereochemistry at certain stereocenters, etc. For some compounds further separation of isomers and / or a...
example 1
[0746] Example 1, Compound 1
[0747] Two of N-(2-chloro-3-fluorobenzoyl)-O-(4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl)homoserine kind of synthesis Example 1a
[0748]
[0749] Compound 1a-a: at 0 °C and under N 2 To a solution of tert-butyl 7-(4-hydroxybutyl)-3,4-dihydro-2H-1,8-naphthyridine-1-carboxylate (11 g, 35.90 mmol) in DMF (150 mL) NaH (2.15 g, 53.85 mmol, 60% suspension in mineral oil) was added. The mixture was stirred at 0°C for 30 minutes, and then 3-bromoprop-1-ene (5.21 g, 43.08 mmol, 1.2 equiv) was added to the mixture at 0°C. The mixture was stirred at 20°C for 10 hours. TLC (petroleum ether / ethyl acetate=3 / 1, R f = 0.1) indicated complete consumption of tert-butyl 7-(4-hydroxybutyl)-3,4-dihydro-2H-1,8-naphthyridine-1-carboxylate (11 g, 35.90 mmol). LCMS indicated detection of the desired M+H + . The mixture was treated with NH 4 The Cl solution was quenched and extracted with EtOAc (3 x 50 mL). The organic layer was washed with brine an...
example 2
[0768] Example 2, compound 8
[0769] 2-(2-Ethylbutanylamino)-5-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy)pentanoic acid
[0770]
[0771]Compound 2a: Two batches in parallel: To a mixture of ethyl 4-oxopentanoate (50 g, 346.82 mmol, 49.50 mL) and 2-aminopyridine-3-carbaldehyde (42.35 g, 346.82 mmol) in EtOH (800 mL) L-Proline (19.96 g, 173.41 mmol) was added. The mixture was refluxed at 85°C for 12 hours. LCMS indicated the reaction was complete. TLC (petroleum ether / ethyl acetate=2:1, R f =0.31) is the spot of the product. The mixtures were combined and concentrated under reduced pressure. H 2 O (1000 mL) and EtOAc (3 x 800 mL), washed with brine and washed with Na 2 SO 4 Dry, filter and concentrate under reduced pressure. The crude product was subjected to column chromatography (SiO 2 , petroleum ether / ethyl acetate=10 / 1 to 1:1) to obtain compound 2a (60 g, 240.85 mmol, 34.72% yield, 92.4% purity) as a yellow solid. LCMS(ESI+):m / z=231.1(M+H) + ,RT=...
PUM
| Property | Measurement | Unit |
|---|---|---|
| wavelength | aaaaa | aaaaa |
| chirality | aaaaa | aaaaa |
| chirality | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to View More