ChemicalBook CAS DataBase List Lurasidone hydrochloride

Lurasidone hydrochloride synthesis

10synthesis methods

Product Name:Lurasidone hydrochloride
CAS Number:367514-88-3
Molecular formula:C28H37ClN4O2S
Molecular Weight:529.14

Lurasidone is an atypical antipsychotic drug discovered and developed by Sumitomo Pharmaceutical for the treatment of patients with schizophrenia. It can be synthesized by condensation reaction of (3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM]Methanesulfonate and (3aR,4S,7R,7aS)4,7 -Methano-1H-isoindole-1,3(2H)-dione.

(3aR,7aR)-4'-(1,2-Benzisothiazol-3-yl)octahydrospiro[2H-isoindole-2,1'-piperaziniuM] Methanesulfonate

186204-37-5
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14805-29-9 Synthesis

(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione

14805-29-9
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367514-88-3
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Yield:367514-88-3 98.3%

Reaction Conditions:

Stage #1: (3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate;(3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dionewith potassium carbonate in toluene at 105; for 15 h;Industrial scale;
Stage #2: with hydrogenchloride in isopropyl alcohol;Industrial scale;

Steps:

8 industrial synthesis of Lurasidone

Intermediate 4 (28.8 kg, 66.2 mol), intermediate 5 (12.0 kg, 72.8 mol) andpotassium carbonate (11.0 kg, 79.7 mol) are suspended in toluene (270 1), and theresulting suspension is heated at 105°C for 15 hours, monitoring the reaction by UPLC. When the reaction is complete, the mixture is left to cool at room temperature, and water (90 1) is added. The phases are separated, the organic solution is concentrated to a small volume, and Lurasidone is isolated as thehydrochloride after treatment with HCI in isopropanol (34.4 kg, yield 98.3%, purity [HPLCJ 99.49%).

References:

WO2015/56205,2015,A1 Location in patent:Page/Page column 14