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. 2022 Oct 17;65(20):13629–13644. doi: 10.1021/acs.jmedchem.2c00921

Scheme 1. Synthesis of Sebetralstat.

Scheme 1

Reagents and conditions: (a) 2-Hydroxypyridine (1.2 equiv), K2CO3 (3.0 equiv), acetone, 50 °C, 18 h, 78%; (b) methanesulfonyl chloride (1.3 equiv), Et3N, (1.4 equiv), dichloromethane, rt, 18h, 93%; (c) methyl 3-(methoxymethyl)-1H-pyrazole-4-carboxylate (0.83 equiv), K2CO3 (2.0 equiv), DMF, 60 °C, 18 h, 54%; (d) NaOH (3.0 equiv), THF-MeOH-H2O, rt, 18 h, 34%; (e) 22a (1.0 equiv), C-(3-fluoro-4-methoxy-pyridin-2-yl)-methylamine (1.0 equiv), HATU (1.1 equiv), Et3N (6.0 equiv), dichloromethane, rt, 4 h, 64%.