ChemicalBook CAS DataBase List ITI-722

ITI-722 synthesis

7synthesis methods

Product Name:ITI-722
CAS Number:313368-91-1
Molecular formula:C24H28FN3O
Molecular Weight:393.5

ITI-722 is a first-in-class dual 5HT2A receptor antagonist and dopamine receptor phosphoprotein modulator (DPPM).

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

Li, Peng; Zhang, Qiang; Robichaud, Albert J.; Lee, Taekyu; Tomesch, John; Yao, Wei; Beard, J. David; Snyder, Gretchen L.; Zhu, Hongwen; Peng, Youyi; Hendrick, Joseph P.; Vanover, Kimberly E.; Davis, Robert E.; Mates, Sharon; Wennogle, Lawrence P. Discovery of a Tetracyclic Quinoxaline Derivative as a Potent and Orally Active Multifunctional Drug Candidate for the Treatment of Neuropsychiatric and Neurological Disorders. Journal of Medicinal Chemistry. Intra-Cellular Therapies, Inc. New York, USA 10032Volume 57. Issue 6. Pages 2670-2682. 2014.

313368-85-3 Synthesis

(6bR,10aS)-3-Methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline

313368-85-3
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40862-32-6
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313368-91-1
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Yield:313368-91-1 84%

Reaction Conditions:

with caesium carbonate in acetonitrile at 20; for 24 h;Reagent/catalyst;Solvent;Temperature;

Steps:

9; 10 Method B

0.459 g (2.0 mmol) formula (II) compound is dissolved in 15 ml acetonitrile, then, to this, 1.303 g (4.0 mmol) caesium carbonate and 0.876 g (3.0 mmol) 4-iodo-4'-fluoro butyrophenone is added. The reaction mixture is stirred for 24 hours at room temperature. Then it is filtered and evaporated. The evaporation residue is dissolved in 20 ml dichlorom ethane and then extracted with 10 ml water, than with 10 ml saturated NaCl solution. The organic phase is dried on Na₂S0₄, filtered and evaporated. The 1.06 g raw product obtained is cleaned on silica gel with flash chromatography using CfTCb-MeOH as eluent. 0.66 g (84%) formula (I) compound is obtained (light brown oil).

References:

WO2019/102240,2019,A1 Location in patent:Page/Page column 75; 76