US 11,697,736 B2
Silicon containing detectable compounds
Ronald Graham, Carlsbad, CA (US); and Rodrigo Rodriguez, San Diego, CA (US)
Assigned to SINGULAR GENOMICS SYSTEMS, INC., San Diego, CA (US)
Filed by SINGULAR GENOMICS SYSTEMS, INC., San Diego, CA (US)
Filed on May 17, 2019, as Appl. No. 16/415,700.
Claims priority of provisional application 62/673,579, filed on May 18, 2018.
Prior Publication US 2019/0352508 A1, Nov. 21, 2019
Int. Cl. C09B 11/24 (2006.01); C09B 69/00 (2006.01); C07F 7/08 (2006.01); C07H 23/00 (2006.01)
CPC C09B 11/24 (2013.01) [C07F 7/083 (2013.01); C07F 7/0803 (2013.01); C07F 7/0825 (2013.01); C09B 69/008 (2013.01); C07F 7/0816 (2013.01); C07H 23/00 (2013.01)] 20 Claims
OG exemplary drawing
 
1. A method of making a compound, or salt thereof, having the formula:

OG Complex Work Unit Chemistry
said method comprising mixing compound A, compound B, and compound C in a reaction vessel, wherein
compound A has the formula:

OG Complex Work Unit Chemistry
compound B is a coupling reagent;
compound C has the formula:

OG Complex Work Unit Chemistry
wherein
R1, R4, R5, R6, and R7 are independently hydrogen, halogen, —CF3, —CBr3, —CCl3, —CI3, —CHF2, —CHBr2, —CHCl2, —CHI2, —CH2F, —CH2Br, —CH2Cl, —CH2I, —OH, —NH2, —COOH, —CONH2, —SH, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R2 and R3 are independently substituted or unsubstituted alkyl, or substituted or unsubstituted heteroalkyl;
R8 is hydrogen or a bioconjugate reactive moiety;
R9, R10, R11, R12 are independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted heteroalkyl;
R13 is a leaving group;
L1 and L2 are independently a bond or a covalent linker;
R4 and R5 substituents bonded to the same nitrogen atom may optionally be joined to form a substituted or unsubstituted heterocycloalkyl, or substituted or unsubstituted heteroaryl;
R6 and R7 substituents bonded to the same nitrogen atom may optionally be joined to form a substituted or unsubstituted heterocycloalkyl, or substituted or unsubstituted heteroaryl;
R4 and R9 substituents may optionally be joined to form a substituted or unsubstituted heterocycloalkyl, or substituted or unsubstituted heteroaryl;
R7 and R10 substituents may optionally be joined to form a substituted or unsubstituted heterocycloalkyl, or substituted or unsubstituted heteroaryl;
R5 and R11 substituents may optionally be joined to form a substituted or unsubstituted heterocycloalkyl, or substituted or unsubstituted heteroaryl; and
R6 and R12 substituents may optionally be joined to form a substituted or unsubstituted heterocycloalkyl, or substituted or unsubstituted heteroaryl.