N-alkylation of acridans
AssigneeSiemens Healthcare Diagnostics Inc.
InventorAnand Natrajan
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Abstract
The present invention provides compounds used in the synthesis of chemiluminescent acridinium compounds and methods of producing these compounds. Specifically, methods are provided for the N-alkylation of acridan compounds using alkylating reagents. Typically, these alkylating reagents comprise a protected sulfonate group protected with an acid-labile protecting group.
Claims16
A method for the N-alkylation of an acridan compound comprising reacting said acridan compound with a protected sulfonate triflate compound having the structure of formula (R1):
- wherein G is an acid-labile protecting group;
- and
- —RL— is independently selected at each occurrence from C1-20 linear or branched bivalent hydrocarbon radicals;
- optionally substituted with one or more (e.g., 1-5, one, two, three, four, five) heteroatoms (e.g., O, S, N, P, F, Cl, Br, I), and combinations thereof, and wherein RL optionally comprises a zwitterionic linker group (e.g., —ZL—).
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-31. (canceled)
A method for synthesis of an acridinium comprising:
- (a) reducing an acridine compound having the structure:
- to produce an acridan having the structure:
- (b) reacting said acridan with a first protected sodium triflate compound having the structure:
- to produce an N-alkylacridan having the structure:
- and
- (c) oxidizing said N-alkylacridan to produce an N-alkylacridinium having the structure:
- wherein “m” and “n” are independently 0-4 and at least one of “m” or “n” is greater than 0;
- R1 and R2 are independently selected from electron donating groups;
- R3 is hydrogen or a C1-C45 hydrocarbon radical optionally substituted with one or more (e.g., 1-20) heteroatoms (e.g., O, S, N, P, F, Cl, Br, I) and wherein R3 may optionally comprise a zwitterionic group (e.g. —Z) and/or a zwitterionic linker group (e.g., —ZL—);
- —RL— is independently selected at each occurrence from C1-20 linear or branched bivalent hydrocarbon radicals;
- optionally substituted with one or more (e.g., 1-5) heteroatoms (e.g., O, S, N, P, F, Cl, Br, I, etc.), and combinations thereof, and wherein RL optionally comprises a zwitterionic linker group (e.g., —ZL—);
- and
- G is an acid-labile protecting group.
-41. (canceled)
An N-alkylated acridan compound having the structure according to formula (NA1):
(canceled)
An N-alkylated acridinium compound having the structure according to formula (NA2):
(canceled)
Dependencies are inferred from the claim text.