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ChemicalBook CAS DataBase List Azelnidipine
123524-52-7

Azelnidipine synthesis

3synthesis methods
A solution of benzhydrylamine (46) and epichlorohydrin (47) was mixed without adding solvent to give azetidinol 48 in 57% yield. DCC coupling between cyanoacetic acid (49) and azetidinol 48 in hot THF gave ester 50 in 93% yield. Cyanoester 50 was treated with ethanol and HCl gas in chloroform to give imidate HCl salt 51, which was treated with ammonia gas in chloroform and ammonium acetate in acetonitrile to give the corresponding amidinoacetate 52. A modified Hantzsch reaction was employed to construct the 2-amino-1,4- dihydropyridine core structure. Compound 52 was condensed with 2-(3-nitrobenzylidene)acetic acid isopropyl ester (55) in the presence of NaOMe in refluxing isopropanol to give the cyclized product, azelnidipine (V) in 74% yield. Benzylideneacetoacetate 55 was obtained through the Knoevenagel reaction employing 3-nitrobenzaldehyde (53) and isopropyl acetoacetate (54) in isopropanol containing a catalytic amount of piperidinium acetate at 45-55oC in 65% yield.

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Yield:-

Steps:

Multi-step reaction with 4 steps
1: acetic acid; piperidine / ethanol / 24 h / 20 - 30 °C
2: potassium hydroxide / ethanol; water / 6 h / Reflux
3: dicyclohexyl-carbodiimide / tetrahydrofuran / 10 h / 60 - 70 °C
4: sodium methylate / ethanol / 6 h / Reflux

References:

WEIHAI DISU PHARM CO LTD;Weihai Dijia Pharmaceutical Co., Ltd.;GUAN, XITAO;LIANG, SONGJUN;CAO, DEQIANG;LI, LULU;MIAO, HUAMING CN105461691, 2016, A

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