US 12,441,721 B2
Synthesis of heterocyclic compounds from carboxamide and carboxamide derivatives with haloalkanols
Rajshekhar Karpoormath, KwaZulu-Natal (ZA); and Nisar Sayyad, KwaZulu-Natal (ZA)
Assigned to University of KwaZulu-Natal, KwaZulu-Natal (ZA)
Appl. No. 18/017,201
Filed by University of KwaZulu-Natal, KwaZulu-Natal (ZA)
PCT Filed Jul. 21, 2021, PCT No. PCT/IB2021/056583
§ 371(c)(1), (2) Date Jan. 20, 2023,
PCT Pub. No. WO2022/018651, PCT Pub. Date Jan. 27, 2022.
Claims priority of application No. 202021031239 (IN), filed on Jul. 21, 2020.
Prior Publication US 2023/0295139 A1, Sep. 21, 2023
Int. Cl. C07D 413/04 (2006.01); C07D 263/10 (2006.01); C07D 263/12 (2006.01); C07D 263/14 (2006.01); C07D 265/08 (2006.01); C07D 273/01 (2006.01); C07D 273/04 (2006.01)
CPC C07D 413/04 (2013.01) [C07D 263/10 (2013.01); C07D 263/12 (2013.01); C07D 263/14 (2013.01); C07D 265/08 (2013.01); C07D 273/01 (2013.01); C07D 273/04 (2013.01)] 12 Claims
 
1. A method for the synthesis of a compound of the Formula (II)

OG Complex Work Unit Chemistry
the method comprising reacting a carboxamide or carboxamide derivative of the Formula (IIa)

OG Complex Work Unit Chemistry
with a substituted alkanol of the Formula (IIb)

OG Complex Work Unit Chemistry
wherein,
X is selected from the group consisting of NH2, NHR4, and OH;
X1 is selected from the group consisting of NH, O, and NR4;
R1 is selected from the group consisting of hydrogen and optionally substituted linear or branched C1-C10 alkyl;
R2 is selected from the group consisting of hydrogen and optionally substituted linear or branched C1-C12 alkyl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, and optionally substituted aryl;
R is selected from the group consisting of hydrogen, optionally substituted linear or branched alkyl, optionally substituted linear or branched alkenyl, optionally substituted linear or branched alkoxy, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted aryl, and optionally substituted heteroaryl,
Z is siloxyl, methanesulphonate, para-toluenesulfonate, or a halogen atom selected from the group consisting of Br, CI, I and F,
R4 is optionally substituted alkyl; and
wherein the method comprises providing the carboxamide or carboxamide derivative and the substituted alkanol in a single reaction vessel to form a reaction mixture, and heating the reaction mixture at a temperature of about 100° C. to about 160° C. to yield the compound of the Formula (II).