US 11,731,962 B2
LpxC inhibitor and methods of making
Min Teng, San Diego, CA (US); Baskar Nammalwar, San Diego, CA (US); and David T. Puerta, San Diego, CA (US)
Assigned to BLACKSMITH MEDICINES, INC., San Diego, CA (US)
Filed by Blacksmith Medicines, Inc., San Diego, CA (US)
Filed on Mar. 24, 2021, as Appl. No. 17/211,029.
Claims priority of provisional application 63/153,152, filed on Feb. 24, 2021.
Claims priority of provisional application 62/994,654, filed on Mar. 25, 2020.
Prior Publication US 2021/0309651 A1, Oct. 7, 2021
Int. Cl. C07D 413/14 (2006.01)
CPC C07D 413/14 (2013.01) 18 Claims
 
1. A process for the preparation of Formula 15:

OG Complex Work Unit Chemistry
wherein X is halogen, —OTf, —OTs, or —OMs; and
each PG is methyl, benzyl, p-methoxybenzyl, methoxymethyl, [2-(trimethylsilyl)ethoxylmethyl, triisopropylsilyl, or tert-butyldimethylsilyl; comprising:
(1) contacting the compound of Formula 14:

OG Complex Work Unit Chemistry
wherein X is halogen, —OTf, —OTs, or —OMs; and
each PG is methyl, benzyl, p-methoxybenzyl, methoxymethyl, [2-(trimethylsilyl)ethoxylmethyl, triisopropylsilyl, or tert-butyldimethylsilyl;
with a suitable oxidation reagent system in a suitable solvent to provide a compound of Formula 15;
wherein:
the suitable oxidation reagent system of step (1) is Collins reagent, pyridinium dichromate, pyridinium chlorochromate, Dess-Martin periodinane, 2-iodobenzoic acid, a TPAP/NMO system, or a TEMPO/bleach system; and
the suitable solvent of step (1) is acetonitrile, dimethylsulfoxide, dichloromethane, chloroform, dichloroethane, hexanes, ethyl acetate, acetic acid, toluene, water, or a combination thereof.