6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol -Drug Synthesis Database

【结构式】

【分子编号】67992

【品名】6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol

【CA登记号】　

【分子式】C₁₀H₁₃BrN₄O

【分子量】285.144

【元素组成】C 42.12% H 4.60% Br 28.02% N 19.65% O 5.61%

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：(IV)

Condensation of 2-amino-3,5-dibromopyrazine (I) with neat 3-amino-pentane (II) under microwave irradiation at 150 °C yields the diaminopyrazine (III), which is then subjected to cyclization with CDI in refluxing THF to give 6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol (IV). Sonogashira cross-coupling of aryl bromide (IV) with (trimethylsilyl)acetylene (V) in the presence of PdCl2(PPh3)2, CuI and Et3N in DMF at 80 °C affords adduct (VI), which is finally desilylated by treatment with KF in MeOH/THF/H2O .

参考文献中间体

合成目标

【1】 Muci, A., Finer, J.T., Lu, P.-P., Russell, A.J., Morgan, B.P., Morgans, D.J. Jr. (Cytokinetics, Inc.). Certain chemical entities, compositions and methods. EP 2069352, JP 2009545596, US 2008146561, US 7598248, US 8227603, US 8299248, WO 200801669.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	26178	3,5-dibromo-2-pyrazinamine	24241-18-7	C₄H₃Br₂N₃	详情	详情
(II)	25924	1-ethylpropylamine; 3-pentanamine	616-24-0	C₅H₁₃N	详情	详情
(III)	67991	6-bromo-N²-(pentan-3-yl)pyrazine-2,3-diamine		C₉H₁₅BrN₄	详情	详情
(IV)	67992	6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol		C₁₀H₁₃BrN₄O	详情	详情
(V)	23897	ethynyl(trimethyl)silane；trimethylsilyl acetylene	1066-54-2	C₅H₁₀Si	详情	详情
(VI)	67993	1-(pentan-3-yl)-6-((trimethylsilyl)ethynyl)-1H-imidazo[4,5-b]pyrazin-2-ol		C₁₅H₂₂N₄OSi	详情	详情

Extended Information