CP-226,269

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 D4 receptors in the brain.[1][2]

CP-226,269
Identifiers
IUPAC name
  • 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
FormulaC18H19FN4
Molar mass310.376 g·mol−1
3D model (JSmol)
SMILES
  • n4ccccc4N3CCN(CC3)Cc2cc1cc(F)ccc1[nH]2
InChI
  • 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 Y
  • Key:PQOIDBZLMJMYCD-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis

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):[3]

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).

References
  1. Sharma A, Kramer ML, Wick PF, Liu D, Chari S, Shim S, Tan W, Ouellette D, Nagata M, DuRand CJ, Kotb M, Deth RC (May 1999). "D4 dopamine receptor-mediated phospholipid methylation and its implications for mental illnesses such as schizophrenia". Molecular Psychiatry. 4 (3): 235–46. doi:10.1038/sj.mp.4000522. PMID 10395213.
  2. Basso AM, Gallagher KB, Bratcher NA, Brioni JD, Moreland RB, Hsieh GC, Drescher K, Fox GB, Decker MW, Rueter LE (July 2005). "Antidepressant-like effect of D(2/3) receptor-, but not D(4) receptor-activation in the rat forced swim test". Neuropsychopharmacology. 30 (7): 1257–68. doi:10.1038/sj.npp.1300677. PMID 15688083.
  3. Anton Franz Josef Fliri, et al. WO 1999009025 (Pfizer Products Inc).
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