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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed
⚫ | verifiedrevid = 449587261
⚫ | ImageFile=Setoperone.svg
⚫ | ImageSize=250px
⚫ | PIN=6-{2-ethyl}-7-methyl-2,3-dihydro-5''H''-thiazolopyrimidin-5-one
⚫ | OtherNames=

⚫ |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BQ67CS3Q3E | UNII = BQ67CS3Q3E
| CASNo_Ref = {{cascite|correct|??}}
⚫ | verifiedrevid = 437164307
⚫ | CASNo=86487-64-1
⚫ |ImageFile=Setoperone.png
⚫ | PubChem=68604
⚫ |ImageSize=200px
⚫ |IUPACName=6--1-piperidinyl]ethyl]-7-methyl-2,3-dihydrothiazolopyrimidin-5-one
⚫ |OtherNames=
⚫ |Section1={{Chembox Identifiers
⚫ | CASNo=86487-64-1
⚫ | PubChem=68604
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02686 | KEGG = D02686
| SMILES=CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F | SMILES=CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 61870
| 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
| InChIKey = RBGAHDDQSRBDOG-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RBGAHDDQSRBDOG-UHFFFAOYSA-N
}} }}

|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>21</sub>H<sub>24</sub>FN<sub>3</sub>O<sub>2</sub>S | Formula=C<sub>21</sub>H<sub>24</sub>FN<sub>3</sub>O<sub>2</sub>S
| MolarMass=401.50 g/mol | MolarMass=401.50 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}

|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
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| volume = 156 | volume = 156
| pages = 1029–1034 | pages = 1029–1034
| url = http://ajp.psychiatryonline.org/cgi/content/full/156/7/1029 | url = http://ajp.psychiatryonline.org/cgi/content/full/156/7/1029
| pmid = 10401447 | pmid = 10401447
| issue = 7 | issue = 7
| date = July 1, 1999 }}</ref> | date = July 1, 1999 | doi = 10.1176/ajp.156.7.1029
| s2cid = 453720
}}</ref>
or ].<ref>{{Cite journal or ].<ref>{{Cite journal
| author = ], Shitij Kapur, Corey Jones, Jean DaSilva, Gregory M. Brown, Alan A. Wilson, ] and Robert B. Zipursky | author = Ralph Lewis, Shitij Kapur, Corey Jones, Jean DaSilva, Gregory M. Brown, Alan A. Wilson, ] and Robert B. Zipursky
| title = Serotonin 5-HT<sub>2</sub> Receptors in Schizophrenia: A PET Study Using &#91;<sup>18</sup>F&#93;Setoperone in Neuroleptic-Naive Patients and Normal Subjects | title = Serotonin 5-HT<sub>2</sub> Receptors in Schizophrenia: A PET Study Using &#91;<sup>18</sup>F&#93;Setoperone in Neuroleptic-Naive Patients and Normal Subjects
| journal = ] | journal = ]
| volume = 156 | volume = 156
| pages = 72–78 | pages = 72–78
| url = http://ajp.psychiatryonline.org/cgi/content/abstract/156/1/72
| pmid = 9892300 | pmid = 9892300
| issue = 1 | issue = 1
| date = January 1, 1999 }}</ref> | date = January 1, 1999 | doi = 10.1176/ajp.156.1.72
}}</ref>
==Synthesis==
</ref> Patent (Intermediate 11 & Ex 1):<ref>EP0070053 idem Ludo E. J. Kennis, Josephus C. Mertens, {{US patent|4443451}} (1984 to Janssen Pharmaceutica N.V.).</ref> Radiolabelled:<ref>Maziere, B.; Crouzel, C.; Venet, M.; Stulzaft, O.; Sanz, G.; Ottaviani, M.; Sejourne, C.; Pascal, O.; Bisserbe, J.C. (1988). "Synthesis, affinity and specificity of 18F-setoperone, a potential ligand for in-vivo imaging of cortical serotonin receptors". International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology. 15 (4): 463–468. doi:10.1016/0883-2897(88)90018-9.</ref>]]

The starting material is called 6-(2-hydroxyethyl)-7-methyl-2,3-dihydro-thiazolopyrimidin-5-one, ('''1'''). Halogenation of this with hydrobromic acid in acetic acid gives ('''2'''). Sn2 alkylation with 4-(4-fluorobenzoyl)piperidine ('''3''') under Finkelstein reaction conditions affords setoperone ('''4''').

==See also==
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* ]


==References== ==References==
{{Reflist}} {{Reflist}}


{{Serotonergics}} {{Antipsychotics}}


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{{nervous-system-drug-stub}} {{nervous-system-drug-stub}}