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Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271
Graphical Abstract
Figure 1: Chemical structure of Notum inhibitor LP-922056 (1).
Scheme 1: Synthesis of LP-922056 (1). Reagents and conditionsa: (a) (COCl)2 (3.3 equiv), DMF, CH2Cl2, 55 °C ,...
Scheme 2: Chlorination of 6 with N-chlorosuccinimide (NCS). Reagents and conditions: (a) NCS (1.2 equiv), AcO...
Scheme 3: Improved synthesis of 5. Reagents and conditions: (a) NaOMe (5 equiv), 1,4-dioxane, 0 °C then rt, 1...
Figure 2: Concentrations of 1 in mouse following oral administration (p.o.) at 10 mg/kg.
Scheme 4: Preparation of amides 17. Representative reagents and conditionsa: (a) HBTU (1.1 equiv), iPr2NEt (2...