3-{1-[(1R)-3-hydrazino-1-methylpropyl]-1H-imidazol-4-yl}pyridine -Drug Synthesis Database

【结构式】

【分子编号】53100

【品名】3-{1-[(1R)-3-hydrazino-1-methylpropyl]-1H-imidazol-4-yl}pyridine

【CA登记号】n/a

【分子式】C₁₂H₁₇N₅

【分子量】231.30068

【元素组成】C 62.31% H 7.41% N 30.28%

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：(XXIII)

The intermediate hydrazine (XXIII) was obtained by two alternative methods. Alkylation of 4-(3-pyridyl)imidazole (II) with the chiral mesylate (XIX), prepared from (R)-1,3-butanediol (XVIII), furnished, after desilylation with tetrabutylammonium fluoride, the imidazolyl butanol (XX). Condensation of alcohol (XX) with di-tert-butyl azodicarboxylate in the presence of PPh3 yielded the hydrazine dicarboxylate (XXII), which was then deprotected to hydrazine (XXIII) under acidic conditions.

参考文献中间体

合成目标

【1】 Kaneko, T.; McMillen, W.T.; McLaughlin, R.W.; Ripin, D.H.B.; Vanerplas, B.C. (Pfizer Inc.); Synthesis of carbamate ketolide antibiotics. EP 1088828; JP 2001151792 .

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)	17164	3-(1H-imidazol-4-yl)pyridine		C₈H₇N₃	详情	详情
(XVIII)	53095	(R)-(-)-1,3-Butanediol; (R)-(-)-1,3-Butylene glycol; (R)-(-)-1,3-Dihydroxybutane; (R)-1,3-Butanediol	6290-03-5	C₄H₁₀O₂	详情	详情
(XIX)	53096	(1R)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpropyl methanesulfonate	n/a	C₁₁H₂₆O₄SSi	详情	详情
(XX)	53097	(3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]-1-butanol	n/a	C₁₂H₁₅N₃O	详情	详情
(XXI)	53098	Azodicarboxylic acid di-tert-butyl ester	870-50-8	C₁₀H₁₈N₂O₄	详情	详情
(XXII)	53099	di(tert-butyl) 1-{(3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl}-1,2-hydrazinedicarboxylate	n/a	C₂₂H₃₃N₅O₄	详情	详情
(XXIII)	53100	3-{1-[(1R)-3-hydrazino-1-methylpropyl]-1H-imidazol-4-yl}pyridine	n/a	C₁₂H₁₇N₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXIII)

In an alternative synthesis of hydrazine (XXIII), aldehyde (IX) was condensed with tert-butyl hydrazinecarboxylate (XXIV), producing hydrazone (XXV), which was further reduced to the hydrazinecarboxylate (XXVI) in the presence of NaBH(OAc)3. Acidic cleavage of the N-Boc group of (XXVI) provided hydrazine (XXIII).

参考文献中间体

合成目标

【1】 Kaneko, T.; McMillen, W.T.; McLaughlin, R.W.; Ripin, D.H.B.; Vanerplas, B.C. (Pfizer Inc.); Synthesis of carbamate ketolide antibiotics. EP 1088828; JP 2001151792 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	53087	3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butanal	n/a	C₁₂H₁₃N₃O	详情	详情
(XXIII)	53100	3-{1-[(1R)-3-hydrazino-1-methylpropyl]-1H-imidazol-4-yl}pyridine	n/a	C₁₂H₁₇N₅	详情	详情
(XXIV)	10893	tert-butyl 1-hydrazinecarboxylate; tert-butyl carbazate	870-46-2	C₅H₁₂N₂O₂	详情	详情
(XXV)	53101	tert-butyl 2-{(E,3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butylidene}-1-hydrazinecarboxylate	n/a	C₁₇H₂₃N₅O₂	详情	详情
(XXVI)	53102	tert-butyl 2-{(3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl}-1-hydrazinecarboxylate	n/a	C₁₇H₂₅N₅O₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XXIII)

The condensation of anhydro imidazolide (XIII) with the substituted hydrazine (XXIII) generated the cyclic carbamate (XXVII). After acidic cleavage of the cladinose moiety, the resultant ketone (XXVIII) was converted to the O-methyl oxime (XXIX). The title compound was then obtained by Swern oxidation of (XXIX) followed by basic hydrolysis.

参考文献中间体

合成目标

【1】 Kaneko, T.; McMillen, W.T.; McLaughlin, R.W.; Ripin, D.H.B.; Vanerplas, B.C. (Pfizer Inc.); Synthesis of carbamate ketolide antibiotics. EP 1088828; JP 2001151792 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIII)	53090	(2R,3S,7R,9R,10R,11R,12S,13R)-10-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-12-{[(2R,4R,5S,6S)-5-(acetyloxy)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-2-ethyl-9-methoxy-3,5,7,9,11,13-hexamethyl-6,14-dioxooxa-4-cyclotetradecen-3-yl 1H-imidazole-1-carboxylate	n/a	C₄₆H₇₃N₃O₁₅	详情	详情
(XXIII)	53100	3-{1-[(1R)-3-hydrazino-1-methylpropyl]-1H-imidazol-4-yl}pyridine	n/a	C₁₂H₁₇N₅	详情	详情
(XXVII)	53103	(2S,3S,4R,6R)-6-{[(3aS,4R,7R,8S,9R,10R,11R,13R,15R)-10-{[(2S,3R,4S,6R)-3-(acetyloxy)-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-1-({(3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl}amino)tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-8-yl]oxy}-4-methoxy-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate	n/a	C₅₅H₈₆N₆O₁₅	详情	详情
(XXVIII)	53104	(2S,3R,4S,6R)-2-{[(3aS,4R,7R,8S,9S,10R,11R,13R,15R)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-1-({(3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl}amino)tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl]oxy}-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate	n/a	C₄₅H₇₀N₆O₁₁	详情	详情
(XXIX)	53105	(2S,3R,4S,6R)-2-{[(3aS,4R,7R,8S,9S,10R,11R,13R,15R)-4-ethyl-8-hydroxy-11-methoxy-14-(methoxyimino)-3a,7,9,11,13,15-hexamethyl-2,6-dioxo-1-({(3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl}amino)tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl]oxy}-4-(dimethylamino)-6-methyltetrahydro-2H-pyran-3-yl acetate	n/a	C₄₆H₇₃N₇O₁₁	详情	详情

Extended Information