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Dazopride succinate, AHR-5531C(fumarate), AHR-5531D

达佐必利Chemical Name: 4-Amino-5-chloro-N-(1,2-diethyl-4-pyrazolidinyl)-2-methoxybenzamide succinate
CAS No. 70181-03-2 (free base), 81957-25-7 (fumarate (1:1))
项目整合开发状态: Phase II
项目研究机构: Wyeth Consumer Healthcare (Originator)
合成路线:An alternative method of producing the 1,2-diethyl-4aminopyrazolidine (VIII) is by reduction of the corresponding nitro compound (VII),which is derived from 1,3-dimorpholino-2-nitropropane (VI) and 1,2-diethylhydrazine (II).
📌 参考资料/链接:
参考文献标题:Synthesis of 4-nitro-1,2-hydrocarbyl pyrazolidines and process for preparation thereof
文献作者:Lo,Y.S.; Munson,H.R.Jr.(A.H.Robins Co.Inc.)
参考来源:DE 3130833; FR 2490639; FR 2491065; GB 2081713; JP 3204859; JP 57059868; US 4309552; US 4358599

📄 详细内容


合成路线:Dazopride can be prepared by the condensation of the 1,2-diethyl-4-aminopyrazolidine (VIII) with either 4-amino-5-chloro-2-methoxybenzoic acid in the presence of phosphorus trichloride-pyridine or the corresponding mixed anhydride (IX).

参考文献标题:N-(4-Pyrazolidinyl)benzamides and their amino precursors
文献作者:Cale,A.D.Jr.; Lunsfod,C.D.(A.H.Robins Co.Inc.)
参考来源:US 4207327


合成路线:The dialkylation of aqueous N,N'-diacetyl-hydrazine by simultaneous addition of diethyl sulfate and potassium hydroxide so as to maintain a pH of 10.5-11.5 affords N,N'-diacetyl-N,N'-diethylhydrazine,which is hydrolyzed to diethylhydrazine (II) by hydrochloric acid.The pH of the acid solution is adjusted to 10,where it is maintained during the addition of epichlorohydrin to give 1,2-diethyl-4-pyrazolidinol (III).The pyrazolidinol is converted to 1,2-diethyl 4-aminopyrazolidine (VIII) by either amination of the corresponding chloro compound (IV) or displacement of the mesyloxy group in compound (V) by the azide ion,followed by reduction.

参考文献标题:Process for the preparation of 4-Pyrazolidinols
文献作者:Cale,A.D.Jr.; Jenkins,H.(A.H.Robins Co.Inc.)
参考来源:DE 2031489; ES 380355; FR 2053022; GB 1309018; US 3660426


合成路线:The dialkylation of aqueous N,N'-diacetyl-hydrazine by simultaneous addition of diethyl sulfate and potassium hydroxide so as to maintain a pH of 10.5-11.5 affords N,N'-diacetyl-N,N'-diethylhydrazine,which is hydrolyzed to diethylhydrazine (II) by hydrochloric acid.The pH of the acid solution is adjusted to 10,where it is maintained during the addition of epichlorohydrin to give 1,2-diethyl-4-pyrazolidinol (III).The pyrazolidinol is converted to 1,2-diethyl 4-aminopyrazolidine (VIII) by either amination of the corresponding chloro compound (IV) or displacement of the mesyloxy group in compound (V) by the azide ion,followed by reduction.

合成路线:An alternative method of producing the 1,2-diethyl-4aminopyrazolidine (VIII) is by reduction of the corresponding nitro compound (VII),which is derived from 1,3-dimorpholino-2-nitropropane (VI) and 1,2-diethylhydrazine (II).

合成路线:Dazopride can be prepared by the condensation of the 1,2-diethyl-4-aminopyrazolidine (VIII) with either 4-amino-5-chloro-2-methoxybenzoic acid in the presence of phosphorus trichloride-pyridine or the corresponding mixed anhydride (IX).

参考文献标题:Dazopride succinate
文献作者:Cale,A.Jr.
参考来源:Drugs Fut 1985,10(7),553


合成路线:The dialkylation of aqueous N,N'-diacetyl-hydrazine by simultaneous addition of diethyl sulfate and potassium hydroxide so as to maintain a pH of 10.5-11.5 affords N,N'-diacetyl-N,N'-diethylhydrazine,which is hydrolyzed to diethylhydrazine (II) by hydrochloric acid.The pH of the acid solution is adjusted to 10,where it is maintained during the addition of epichlorohydrin to give 1,2-diethyl-4-pyrazolidinol (III).The pyrazolidinol is converted to 1,2-diethyl 4-aminopyrazolidine (VIII) by either amination of the corresponding chloro compound (IV) or displacement of the mesyloxy group in compound (V) by the azide ion,followed by reduction.

合成路线:Dazopride can be prepared by the condensation of the 1,2-diethyl-4-aminopyrazolidine (VIII) with either 4-amino-5-chloro-2-methoxybenzoic acid in the presence of phosphorus trichloride-pyridine or the corresponding mixed anhydride (IX).
参考文献标题:Synthetic and pharmacological properties of N-(1,2-dialkyl-4-pyrazolidinyl)benzamides - Selective gastric prokinetic agents
文献作者:Munson,H.R.Jr.; Cale,A.D.Jr,Lo,Y.S.; Lunsford,C.D.
参考来源:187th ACS Natl Meet (April 8-13,St.Louis) 1984,7(9),650


产品链接: CAS No. 70181-03-2››

产品链接: CAS No.81957-25-7››