【结 构 式】 |
【分子编号】25924 【品名】1-ethylpropylamine; 3-pentanamine 【CA登记号】616-24-0 |
【 分 子 式 】C5H13N 【 分 子 量 】87.16496 【元素组成】C 68.9% H 15.03% N 16.07% |
合成路线1
该中间体在本合成路线中的序号:(V)The cyclization of 5-amino-4-(4-methoxy-2-methylphenyl)-3-methylpyrazole with ethyl acetoacetate (II) in refluxing acetic acid gives 7-hydroxy-3-(4-methoxy-2-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidine (III), which is treated with POCl3 and diethylaniline in refluxing toluene yielding the corresponding chloro derivative (IV). Finally, this compound is treated with pentyl-3-amine in DMSO at 150 C.
【1】 Arvanitis, A.G.; Chorvat, R.J. (DuPont Pharmaceuticals Co.); Azolo triazines and pyrimidines. US 6124289; WO 9803510 . |
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) | 25921 | 4-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine; 4-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrazol-5-ylamine | C12H15N3O | 详情 | 详情 | |
(II) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate;Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
(III) | 25922 | 3-(4-methoxy-2-methylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol | C16H17N3O2 | 详情 | 详情 | |
(IV) | 25923 | 7-chloro-3-(4-methoxy-2-methylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine; 4-(7-chloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-3-methylphenyl methyl ether | C16H16ClN3O | 详情 | 详情 | |
(V) | 25924 | 1-ethylpropylamine; 3-pentanamine | 616-24-0 | C5H13N | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(II)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 .
【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 |