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【结 构 式】 
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【分子编号】65622 【品名】1-(4-Nitrophenyl)-2-piperidinone 【CA登记号】38560-30-4 |
【 分 子 式 】C11H12N2O3 【 分 子 量 】220.22796 【元素组成】C 59.99% H 5.49% N 12.72% O 21.79% |
合成路线1
该中间体在本合成路线中的序号：(XVIIa)The precursor dihydropyridones (IIa) and (IIb) can be synthesized as follows. Acylation of either 4-nitroaniline (XVa) (1) or 4-iodoaniline (XVb) (2) with 5-bromovaleryl chloride (V) affords the corresponding bromoamides (XVIa) and (XVIb), which are cyclized to piperidones (XVIIa) and (XVIIb) upon treatment with potassium tert-butoxide or with potassium hydroxide under phase-transfer conditions. Piperidones (XVIIa/b) are then chlorinated by means of phosphorus pentachloride in chlorobenzene or chloroform to form the geminal dichlorides (XVIIIa) and (XVIIIb) (1, 2). Dehydrohalogenation of (XVIIIa) by means of lithium carbonate and lithium chloride in DMF at 105-110 °C then provides the chloro dihydropyridone (IIa) (1). Alternatively, the dichloro derivative (XVIIIb) is refluxed with neat morpholine (XIX) to furnish intermediate (IIb) (2). Scheme 3.
| 【1】 Shapiro, R., Rossano, L.T., Mudryk, B.M. et al. (Bristol-Myers Squibb Co.). Process for preparing 4,5-dihydro-pyrazolo[3,4-c]pyrid-2-ones. WO 2007001385. |
| 【2】 Pinto, D., Quan, M., Orwat, M. et al. (Bristol-Myers Squibb Co.). Lactam-containing compounds and derivatives thereof as factor Xa inhibitors. EP 1427415, JP 2005507889, WO 03026652. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVA) | 15547 | 4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline | 100-01-6 | C6H6N2O2 | 详情 | 详情 |
| (XVB) | 26393 | 4-iodoaniline; 4-iodophenylamine | 540-37-4 | C6H6IN | 详情 | 详情 |
| (XVIa) | 65620 | C11H13BrN2O3 | 详情 | 详情 | ||
| (XVIb) | 65621 | C11H13BrINO | 详情 | 详情 | ||
| (XVIIa) | 65622 | 1-(4-Nitrophenyl)-2-piperidinone | 38560-30-4 | C11H12N2O3 | 详情 | 详情 |
| (XVIIb) | 65618 | 1-(4-Iodophenyl)-2-piperidinone | 385425-15-0 | C11H12INO | 详情 | 详情 |
| (XVIIIa) | 65623 | 3,3-Dichloro-1-(4-nitrophenyl)-2-piperidinone | 881386-01-2 | C11H10Cl2N2O3 | 详情 | 详情 |
| (XVIIIb) | 65624 | 3,3-Dichloro-1-(4-iodophenyl)piperidin-2-one | 545445-10-1 | C11H10Cl2INO | 详情 | 详情 |
| (IIA) | 65610 | 3-Chloro-5,6-dihydro-1-(4-nitrophenyl)-2(1H)-pyridinone | 536760-29-9 | C11H9ClN2O3 | 详情 | 详情 |
| (IIB) | 65611 | 1-(4-Iodophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one; N-(4-Iodophenyl)-3-morpholino-5,6-dihydro-2H-pyridin-2-one | 473927-69-4 | C15H17IN2O2 | 详情 | 详情 |
| (V) | 39700 | 5-bromopentanoyl chloride | 4509-90-4 | C5H8BrClO | 详情 | 详情 |
| (XIX) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |