Relicpixant

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Relicpixant

CAS 2445366-94-7

MF C₂₀H₁₉ClF₂N₄O₅S, Mw 500.9 g/mol

methyl (2S)-2-{[7-chloro-2-(2,6-difluoro-4-sulfamoylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl}morpholine-4-
carboxylate
purinoreceptor (P2X) antagonist, 3NWJ8FHG2R

Relicpixant is a small molecule drug. The usage of the INN stem ‘-pixant’ in the name indicates that Relicpixant is a purinoreceptor (P2X) antagonist. Relicpixant has a monoisotopic molecular weight of 500.07 Da.

SYN

US20240034729,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US393005051&_cid=P10-MMH5CF-50302-1

Example 172

Step (8) Preparation of methyl (S)-2-((7-chloro-2-(2,6-difluoro-4-sulfamoylphenyl)imidazo[1,2-a]pyridin-3-yl)methyl)morpholine-4-carboxylate

Aqueous ammonia (2 mL) was diluted with acetonitrile (1 mL) and added dropwise to the above reaction system at 0° C. The reaction system was reacted at room temperature for 0.5 h. The starting material was consumed completely, and a target product was generated as detected by LCMS. The reaction system was extracted with water and ethyl acetate twice, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative chromatography to give compound 172 (185 mg, 99.74% purity) in the form of a white solid. LC-MS: [M+H] ⁺=501.1.

¹H NMR (400 MHZ, DMSO-d ₆) δ=8.11 (d, J=7.4, 1H), 7.29 (d, J=1.6, 1H), 7.22 (s, 2H), 7.14 (d, J=6.6, 2H), 6.60 (dd, J=7.4, 2.1, 1H), 3.33 (d, J=12.8, 1H), 3.13 (d, J=11.3, 2H), 3.07 (s, 3H), 2.97 (d, J=7.8, 1H), 2.77-2.69 (m, 1H), 2.69-2.61 (m, 1H), 2.53 (dd, J=15.5, 8.3, 1H).

PAT

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Example 1: Preparation of Compound of Formula A

To the above reaction mixture was added dropwise ammonia water (2 mL) diluted with acetonitrile (1 mL) at 0° C., and reaction mixture was reacted at room temperature for 0.5 hours. The raw material completely disappeared, and a target product was generated, as shown by LC-MS. The reaction mixture was extracted twice with water and ethyl acetate, washed with brine solution, dried over anhydrous sodium sulfate, concentrated, and purified by C18 chromatography column (water/acetonitrile, RRt=22.5 min). Compound A in an amorphous state (compound A is the compound of formula A) (185 mg, purity: 99.74%) was obtained as a white solid. LC-MS: [M+H]=501.1.

¹H NMR (400 MHz, DMSO-d ₆) δ=8.11 (d, J=7.4, 1H), 7.29 (d, J=1.6, 1H), 7.22 (s, 2H), 7.14 (d, J=6.6, 2H), 6.60 (dd, J=7.4, 2.1, 1H), 3.33 (d, J=12.8, 1H), 3.13 (d, J=11.3, 2H), 3.07 (s, 3H), 2.97 (d, J=7.8, 1H), 2.77-2.69 (m, 1H), 2.69-2.61 (m, 1H), 2.53 (dd, J=15.5, 8.3, 1H).

Step 6: Preparation of methyl (S)-2-((7-chloro-2-(2,6-difluoro-4-sulfamoylphenyl)imidazo[1,2-a]pyridin-3-yl)methyl)morpholine-4-carboxylate AS ABOVE

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020135771&_cid=P10-MMH5AS-49292-1

PAT