Setoperone

Setoperone is a compound that is a ligand to the 5-HT_2A receptor. It can be radiolabeled with the radioisotope fluorine-18 and used as a radioligand with positron emission tomography (PET). Several research studies have used the radiolabeled setoperone in neuroimaging for the studying neuropsychiatric disorders, such as depression^[1] or schizophrenia.^[2]

Setoperone

Names
Preferred IUPAC name 6-{2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl}-7-methyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Identifiers
CAS Number	86487-64-1 Y
3D model (JSmol)	Interactive image
ChemSpider	61870 N
KEGG	D02686 Y
PubChem CID	68604
UNII	BQ67CS3Q3E Y
CompTox Dashboard (EPA)	DTXSID9057848
InChI InChI=1S/C21H24FN3O2S/c1-14-18(20(27)25-12-13-28-21(25)23-14)8-11-24-9-6-16(7-10-24)19(26)15-2-4-17(22)5-3-15/h2-5,16H,6-13H2,1H3 N Key: RBGAHDDQSRBDOG-UHFFFAOYSA-N N InChI=1/C21H24FN3O2S/c1-14-18(20(27)25-12-13-28-21(25)23-14)8-11-24-9-6-16(7-10-24)19(26)15-2-4-17(22)5-3-15/h2-5,16H,6-13H2,1H3 Key: RBGAHDDQSRBDOG-UHFFFAOYAH
SMILES CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
Properties
Chemical formula	C21H24FN3O2S
Molar mass	401.50 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Synthesis

Synthesis:^[3] Patent (Intermediate 11 & Ex 1):^[4] Radiolabelled:^[5]

The starting material is called 6-(2-hydroxyethyl)-7-methyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one, CID:15586462 (1). Halogenation of this with hydrobromic acid in acetic acid gives CID:15586463 (2). Sn2 alkylation with 4-(4-fluorobenzoyl)piperidine [56346-57-7] (3) under Finkelstein reaction conditions affords setoperone (4).

See also

• Altanserin
• Ketanserin
• Pirenperone
• Ritanserin