Compounds and methods of making compounds
Embodiments of the present disclosure provide for compounds and methods of making compounds such as those shown in FIGS. 1.1 A and 1.1 B having formula 2, 3, 4, 5, 11, and 12 and formula 2′, 4′, and 11′, as well as uses for the compounds for imaging, and the like.
1. A method of making a labeled compound, comprising:
reacting a compound including an isotope (Ist) with a compound having formula 1′,
to form a compound having formula 2′,
and
conducting deprotection on the compound having formula 2′ to form a compound having formula 3,
wherein PG is a protecting group and LG is a leaving group, and wherein R is a compound having a formula selected from the group consisting of R1, R2, R3, R4, R5, and R6:
and wherein R′ is
a compound having a formula selected from the group consisting of R′1, R′2, R′3, R′4, and R′5, wherein Ac is an acetyl group, and Bz is a benzoyl group:
2. The method of claim 1 , wherein the isotope is selected from the group consisting of: 18 F, 131 I, 125 I, 124 I, 123 I, 121 I, 77 Br, and 75 Br.
3. The method of claim 1 , wherein the compound including the isotope is selected from the group consisting of: [ 18 F]KF, [ 131 I]NaI, [ 125 I]NaI, [ 124 I]NaI, [ 123 I]NaI, [ 121 I]NaI, [ 77 Br]NaBr, [ 77 Br]Br 2 , [ 75 Br]NaBr, and [ 75 Br]Br 2 .
4. The method of claim 1 , wherein R is R1 or R2.
5. The method of claim 1 , wherein reacting further includes a reactive compound selected from: 1,4,10-Trioxa-7,13-diaza-cyclopentadecane (K2.1), 4,7,13,16,21-Pentaoxa-1,10-diazabicyclo[8.8.5]tricosane (K2.2.1), 4,7,13,18-Tetraoxa-1,10-diazabicyclo[8.5.5]eicosane (K2.1.1), 5,6-Benzo-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacos-5-ene (k2.2.2B), 4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane (K2.2.2), and a combination thereof.
6. The method of claim 5 , wherein the compound is 4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane (K2.2.2).
7. The method of claim 1 , wherein reacting further includes a solvent selected from the group consisting of: dimethyl sulfoxide (DMSO), acetonitrile, dimethylformamide, and a combination thereof.
8. The method of claim 7 , wherein the solvent is DMSO.
9. The method of claim 1 , wherein the compound having formula 2′ is a compound having formula 11′,
10. The method of claim 9 , wherein the compound having formula 3 is a compound having formula 12,