US 11,873,315 B2
Chiral n-heterocyclic phosphorodiamidic acids (NHPAS) and derivatives as novel Brønsted acid catalysts
Jun Yong Kang, Las Vegas, NV (US); and Hai Huang, Clear Water Bay (HK)
Assigned to THE BOARD OF REGENTS OF THE NEVADA SYSTEM OF HIGHER EDUCATION ON BEHALF OF THE UNIVERSITY OF NEVADA, LAS VEGAS, Las Vegas, NV (US)
Filed by The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas, NV (US)
Filed on Jan. 24, 2022, as Appl. No. 17/583,159.
Application 17/583,159 is a continuation of application No. 16/622,451, granted, now 11,248,014, previously published as PCT/US2018/037868, filed on Jun. 15, 2018.
Claims priority of provisional application 62/568,645, filed on Oct. 5, 2017.
Claims priority of provisional application 62/566,834, filed on Oct. 2, 2017.
Claims priority of provisional application 62/521,086, filed on Jun. 16, 2017.
Prior Publication US 2022/0144868 A1, May 12, 2022
Int. Cl. B01J 31/02 (2006.01); C07F 9/32 (2006.01); C07F 9/40 (2006.01); C07F 9/6584 (2006.01); C07F 9/6553 (2006.01)
CPC C07F 9/65848 (2013.01) [B01J 31/0264 (2013.01); C07F 9/3241 (2013.01); C07F 9/4056 (2013.01); C07F 9/655345 (2013.01); B01J 2231/40 (2013.01); B01J 2531/002 (2013.01)] 9 Claims
 
1. A compound having a structure represented by a formula:

OG Complex Work Unit Chemistry
wherein n is selected from 0 and 1;
wherein R101a is —OH;
wherein R101b is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino, provided that at least one of R101a and R101b is —OH, —SH, or C1-C4 alkylamino;
wherein each of R102a, R102b, and R102c is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
wherein R103 is selected from C4-C8 alkyl and Ar101, provided that when R103 is C4-C8 alkyl, then R101b is —SH, —OH, or C1-C4 alkylamino;
wherein Ar101, when present, is selected from C6-C10 aryl and C5-C6 heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and phenyl;
wherein R104 is selected from C1-C4 alkoxy and phenyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino; and
wherein R105 is C1-C4 alkyl,
provided that when n is 0, R101b is —OH, and R103 is C6 aryl or C6 heteroaryl, then either:
(a) each of R102a and R102b is hydrogen, or
(b) one of R102a and R102b is hydrogen and R104 is not the same as —OR5,
or a pharmaceutically acceptable salt thereof.