1,2-diethyl-4-pyrazolidinamine -Drug Synthesis Database

【结构式】

【分子编号】27385

【品名】1,2-diethyl-4-pyrazolidinamine

【CA登记号】70180-92-6

【分子式】C₇H₁₇N₃

【分子量】143.2322

【元素组成】C 58.7% H 11.96% N 29.34%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(VIII)

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.

参考文献中间体

合成目标

【1】 Munson, H.R. Jr.; Cale, A.D. Jr, Lo, Y.S.; Lunsford, C.D.; Synthetic and pharmacological properties of N-(1,2-dialkyl-4-pyrazolidinyl)benzamides - Selective gastric prokinetic agents. 187th ACS Natl Meet (April 8-13, St. Louis) 1984, 7, 9, 650.
【2】 Cale, A.D.Jr.; Jenkins, H. (A.H. Robins Co. Inc.); Process for the preparation of 4-Pyrazolidinols. DE 2031489; ES 380355; FR 2053022; GB 1309018; US 3660426 .
【3】 Cale, A. Jr.; Dazopride succinate. Drugs Fut 1985, 10, 7, 553.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	10416	(3aS,12bS)-2-Methyl-5-nitro-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole		C₁₇H₁₆N₂O₃	详情	详情
(A)	27379	N'-acetylacetohydrazide	3148-73-0	C₄H₈N₂O₂	详情	详情
(I)	27380	N'-acetyl-N,N'-diethylacetohydrazide		C₈H₁₆N₂O₂	详情	详情
(II)	27381	1,2-diethylhydrazine		C₄H₁₂N₂	详情	详情
(III)	27382	1,2-diethyl-4-pyrazolidinol		C₇H₁₆N₂O	详情	详情
(IV)	27383	4-chloro-1,2-diethylpyrazolidine		C₇H₁₅ClN₂	详情	详情
(V)	27384	1,2-diethyl-4-(methylsulfonyl)pyrazolidine		C₈H₁₈N₂O₂S	详情	详情
(VIII)	27385	1,2-diethyl-4-pyrazolidinamine	70180-92-6	C₇H₁₇N₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

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).

参考文献中间体

合成目标

【1】 Lo, Y.S.; Munson, H.R.Jr. (A.H. Robins Co. Inc.); Synthesis of 4-nitro-1,2-hydrocarbyl pyrazolidines and process for preparation thereof. DE 3130833; FR 2490639; FR 2491065; GB 2081713; JP 3204859; JP 57059868; US 4309552; US 4358599 .
【2】 Cale, A. Jr.; Dazopride succinate. Drugs Fut 1985, 10, 7, 553.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	27381	1,2-diethylhydrazine		C₄H₁₂N₂	详情	详情
(VI)	27386	4-[3-(4-morpholinyl)-2-nitropropyl]morpholine		C₁₁H₂₁N₃O₄	详情	详情
(VII)	27387	1,2-diethyl-4-nitropyrazolidine		C₇H₁₅N₃O₂	详情	详情
(VIII)	27385	1,2-diethyl-4-pyrazolidinamine	70180-92-6	C₇H₁₇N₃	详情	详情
(C)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VIII)

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).

参考文献中间体

合成目标

【1】 Munson, H.R. Jr.; Cale, A.D. Jr, Lo, Y.S.; Lunsford, C.D.; Synthetic and pharmacological properties of N-(1,2-dialkyl-4-pyrazolidinyl)benzamides - Selective gastric prokinetic agents. 187th ACS Natl Meet (April 8-13, St. Louis) 1984, 7, 9, 650.
【2】 Cale, A.D.Jr.; Lunsfod, C.D. (A.H. Robins Co. Inc.); N-(4-Pyrazolidinyl)benzamides and their amino precursors. US 4207327 .
【3】 Cale, A. Jr.; Dazopride succinate. Drugs Fut 1985, 10, 7, 553.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(E)	11229	1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate	541-41-3	C₃H₅ClO₂	详情	详情
(D)	12419	4-Amino-5-chloro-2-methoxybenzoic acid	7206-70-4	C₈H₈ClNO₃	详情	详情
(VIII)	27385	1,2-diethyl-4-pyrazolidinamine	70180-92-6	C₇H₁₇N₃	详情	详情
(IX)	27388	4-Amino-5-chloro-2-methoxybenzoic acid ethoxycarbonyl anhydride		C₁₁H₁₂ClNO₅	详情	详情

Extended Information