tert-butyl 3-iodo-4-pyridinylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】48103

【品名】tert-butyl 3-iodo-4-pyridinylcarbamate

【CA登记号】

【分子式】C₁₀H₁₃IN₂O₂

【分子量】320.12997

【元素组成】C 37.52% H 4.09% I 39.64% N 8.75% O 10%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VIII)

Iodination of 4-aminopyridine (VI), followed by protection with Boc2O, provided the N-Boc iodopyridine (VIII). Piperazinone (XI) was prepared by alkylation of 4-(benzyloxycarbonyl)-2-piperazinone (IX) with propargyl bromide (X). Palladium-catalyzed coupling of propargyl piperazinone (XI) with iodopyridine (VIII) furnished adduct (XII), which was subsequently cyclized to the pyrrolopyridine derivative (XIII) upon treatment with DBU. The benzyloxycarbonyl group of (XIII) was then cleaved by transfer hydrogenolysis to yield the intermediate piperazinone (XIV).

参考文献中间体

合成目标

【2】 Myers, M.R.; Becker, M.R.; Ewing, W.R.; Spada, A.P. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. WO 0032590; WO 0107436 .
【1】 Hanney, B.A.; He, W.; Poli, G.B.; Spada, A.P.; Myers, M.R.; Burns, C.J.; Pauls, H.W.; Jiang, J.Z.; Condon, S.M.; Ewing, W.R.; Becker, M.R.; Li, A.; Choi-Sledeski, Y.M.; Lau, W.F.; Davis, R.S. (Aventis Pharmaceuticals, Inc.); Substd. oxoazaheterocyclyl factor Xa inhibitors. EP 1051176; WO 9937304 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	25661	4-pyridinamine; 4-aminopyridine	5044-74-5	C₅H₆N₂	详情	详情
(VII)	48102	3-iodo-4-pyridinamine; 3-iodo-4-pyridinylamine		C₅H₅IN₂	详情	详情
(VIII)	48103	tert-butyl 3-iodo-4-pyridinylcarbamate		C₁₀H₁₃IN₂O₂	详情	详情
(IX)	48104	benzyl 3-oxo-1-piperazinecarboxylate		C₁₂H₁₄N₂O₃	详情	详情
(X)	11176	3-Bromopropyne; 3-Bromo-1-propyne	106-96-7	C₃H₃Br	详情	详情
(XI)	48105	benzyl 3-oxo-4-(2-propynyl)-1-piperazinecarboxylate		C₁₅H₁₆N₂O₃	详情	详情
(XII)	48106	benzyl 4-(3-[4-[(tert-butoxycarbonyl)amino]-3-pyridinyl]-2-propynyl)-3-oxo-1-piperazinecarboxylate		C₂₅H₂₈N₄O₅	详情	详情
(XIII)	48107	tert-butyl 2-([4-[(benzyloxy)carbonyl]-2-oxo-1-piperazinyl]methyl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate		C₂₅H₂₈N₄O₅	详情	详情
(XIV)	48108	tert-butyl 2-[(2-oxo-1-piperazinyl)methyl]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate		C₁₇H₂₂N₄O₃	详情	详情

Extended Information