Riselcaftor

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Riselcaftor

CAS 2799652-36-9

MF C29H28N2O5S MW 516.61

(2R,4R)-2-(2-methoxy-5-methylphenyl)-N-(2-methylquinoline-5-sulfonyl)-4-phenyloxolane-2-
carboxamide

(2R,4R)-2-(2-methoxy-5-methylphenyl)-N-(2-methylquinolin-5-yl)sulfonyl-4-phenyloxolane-2-carboxamide
cystic fibrosis transmembrane regulator (CFTR)protein modulator, 726GWJ6KQQ

Riselcaftor (Example 33) is a CFTR modulator, with an EC₅₀ of 20.1 nM in human bronchial epithelial cells. Riselcaftor can be used for research of cystic fibrosis.

SYN

US20220211692

https://patentscope.wipo.int/search/en/detail.jsf?docId=US367940046&_cid=P11-MIH63N-23616-1

Example 33

(2R,4R)-2-(2-methoxy-5-methylphenyl)-N-(2-methylquinoline-5-sulfonyl)-4-phenyloxolane-2-carboxamide

The enantiomers of Example 32D (140 mg) were separated by chiral preparative supercritical fluid chromatography (ES Industries AD-H column (21×250 mm, 5 micron) 12.8 mg/mL in 10:1 methanol/diethylamine, 56 g/minutes CO ₂, RT 11.8 minutes) to provide the title compound (84.7 mg, 0.164 mmol, 60.2% yield). ¹H NMR (500 MHz, dimethyl sulfoxide-d ₆) δ ppm 12.07 (s, 1H), 8.80 (d, J=8.9 Hz, 1H), 8.27 (d, J=7.3 Hz, 1H), 8.24 (d, J=8.5 Hz, 1H), 7.90 (t, J=7.9 Hz, 1H), 7.48 (d, J=8.9 Hz, 1H), 7.28-7.22 (m, 3H), 7.21-7.16 (m, 1H), 7.11-7.06 (m, 2H), 7.06-7.01 (m, 1H), 6.63 (d, J=8.3 Hz, 1H), 4.15 (t, J=7.9 Hz, 1H), 3.73 (t, J=8.7 Hz, 1H), 3.21-3.14 (m, 1H), 3.11 (s, 3H), 3.05 (dd, J=13.4, 7.0 Hz, 1H), 2.71 (s, 3H), 2.22 (s, 3H), 1.85 (t, J=11.8 Hz, 1H). MS(APCI+) m/z 517 (M+H) ⁺.

PAT