US 12,269,810 B2
Methods of preparing synthetic cannabichromene and cannabicitran and derivatives thereof
Wen-Chun Zhang, Bogart, GA (US); and Aaron P Honeycutt, Loganville, GA (US)
Assigned to PURISYS, LLC, Athens, GA (US)
Appl. No. 17/997,597
Filed by Purisys, LLC, Athens, GA (US)
PCT Filed Apr. 29, 2021, PCT No. PCT/US2021/029952
§ 371(c)(1), (2) Date Oct. 31, 2022,
PCT Pub. No. WO2021/222609, PCT Pub. Date Nov. 4, 2021.
Claims priority of provisional application 63/019,063, filed on May 1, 2020.
Prior Publication US 2023/0219916 A1, Jul. 13, 2023
Int. Cl. C07D 311/70 (2006.01); C07D 493/04 (2006.01); C07D 493/08 (2006.01)
CPC C07D 311/70 (2013.01) [C07D 493/04 (2013.01); C07D 493/08 (2013.01)] 24 Claims
 
1. A method of preparing a compound of Formula I or II,

OG Complex Work Unit Chemistry
wherein,
R1 is selected from the group consisting of hydroxyl and C1-5alkoxy;
R2 and R4 are in each instance independently selected from the group consisting of hydrogen, —C1-5alkyl, —CF3, cyano, nitro, phenyl, —C(O)R6, —NRaRb, —C(O)OR6, —O—C(O)R6, —O—R6, —O—R6, —C(H)═C(R6)2, —N(H)C(O)R6, halo, —N(R6)3;
wherein, Ra and Rb are each independently hydrogen or C1-5alkyl;
wherein, R6 is hydrogen or C1-5alkyl;
R3 is selected from the group consisting of hydrogen, linear or branched C1-10alkyl;
R5 is selected from the group consisting of hydrogen, C1-5alkyl, C1-5alkenyl and prenyl;
comprising:
dosing at a first temperature above 65° C. a compound of Formula Ia

OG Complex Work Unit Chemistry
wherein, R5 is as described above;
to a first mixture, said first mixture comprising an amine and a compound of Formula Ib

OG Complex Work Unit Chemistry
wherein,
R1a is selected from the group consisting of hydroxyl and C1-5alkoxy;
R2a and R4a are each as described above for R2 and R4;
R3a is selected from the group consisting of hydrogen, linear or branched C1-10alkyl; and
R7 is selected from the group consisting of hydrogen, —C(O)Rc,
wherein Rc is hydrogen or C1-5alkyl;
to form a second mixture; and,
allowing the second mixture to react at a second temperature;
wherein, a compound of Formula I or II is prepared.