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ChemicalBook CAS DataBase List Fasudil hydrochloride
105628-07-7

Fasudil hydrochloride synthesis

12synthesis methods
-

Yield:105628-07-7 89%

Reaction Conditions:

in dichloromethane at 0 - 50; for 2 h;Temperature;

Steps:

34-41 Synthesis of Fasudil Hydrochloride

Take the isoquinoline-5-sulfonyl chloride hydrochloride (36.45g, 138mmol) prepared in Example 19 and put it into 180mL of dichloromethane, place it at 0 and slowly add saturated sodium bicarbonate solution to adjust pH value to neutral, separate extraction, save the organic phase, extract the aqueous phase again with dichloromethane (100mL), combine the organic phases, dry with anhydrous sodium sulfate, and filter to obtain isoquinoline-5-sulfonyl chloride Dichloromethane solution. The obtained isoquinoline-5-sulfonyl chloride solution in dichloromethane was slowly added dropwise to a solution of homopiperazine (30.00g, 300mmol) in dichloromethane (120mL) at 0°C. After the addition, it was placed at 50°C for reaction. After 2h, first add 1mol/L dilute hydrochloric acid to adjust the pH to 4.5, discard the organic phase, extract the water phase twice with dichloromethane (120mL×2), then add 1mol/L dilute sodium hydroxide solution to the water phase to adjust pH to 9.5, add dichloromethane (150mL) to extract, the organic phase is washed with water, saturated brine, dried over anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure to obtain oily hexahydro-1-(5-isoquinolinesulfonyl) )-1H-1,4-diazepine (fasudil). Add the obtained oil to methanol (150mL) and heat to dissolve it, adjust the pH to 5-6 with 12mol/L concentrated hydrochloric acid solution, stir and crystallize at room temperature, obtain a white solid after suction filtration, and dry it to obtain fasudil hydrochloride 40.26g, the yield was 89%, and the HPLC content was 99.99%. (The yield is calculated based on isoquinoline-5-sulfonyl chloride hydrochloride).

References:

CN111909088,2020,A Location in patent:Paragraph 0112-0127

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