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Pfizer brands
CP-226,269
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    CP-226,269

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    CP-226,269
    CP-226,269 Structure.svg
    CP-226,269 3D.gif
    Identifiers
    • 5-fluoro-2-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1H-indole
    CAS Number
    PubChem CID
    IUPHAR/BPS
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C18H19FN4
    Molar mass 310.376 g·mol−1
    3D model (JSmol)
    • n4ccccc4N3CCN(CC3)Cc2cc1cc(F)ccc1[nH]2
    • InChI=1S/C18H19FN4/c19-15-4-5-17-14(11-15)12-16(21-17)13-22-7-9-23(10-8-22)18-3-1-2-6-20-18/h1-6,11-12,21H,7-10,13H2 checkY
    • Key:PQOIDBZLMJMYCD-UHFFFAOYSA-N checkY
     ☒NcheckY (what is this?)  (verify)

    CP-226,269 is a drug which acts as a dopamine agonist selective for the D4 subtype, which is used for researching the role of D4receptors in the brain.

    Synthesis

    UMB38.svg

    The piperazine used has dual use in the synthesis of ABT-724, ABT-670, Azaperone, MLS 1547 [315698-36-3], Revenast [85673-87-6], UMB38 & XH-148.

    Patent (Ex 15):

    Weinreb ketone synthesis between 5-Fluoroindole-2-Carboxylic acid [399-76-8] (1) and N,O-Dimethylhydroxylamine Fb: [1117-97-1] Hcl: [6638-79-5] (2) gives the Weinreb–Nahm amide, 5-Fluoro-N-Methoxy-N-Methyl-Indole-2-Carboxamide, CID:23003585 (3). This intermediate is further reduced giving 5-Fluoro-Indole-2-Carbaldehyde [220943-23-7] (4). Reductive amination with 1-(2-Pyridyl)Piperazine [34803-66-2] (5) completed the synthesis CP-226,269 (6).


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