154590-66-6
基本信息
(S)-N-((3-(3-氟-4-(哌嗪-1-基)苯基)-2-氧噁唑啉丁-5-基)甲基)乙酰胺
N-[[(5S)-3-[3-氟-4-(1-哌嗪基)苯基]-2-氧代-5-恶唑烷基]甲基]乙酰胺
N-[[(5S)-3-[3-Fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
Acetamide,N-[[(5S)-3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-
物理化学性质
| 沸点 | 587.3±50.0 °C(Predicted) |
| 密度 | 1.273±0.06 g/cm3(Predicted) |
| 储存条件 | Storage temp. 2-8°C |
| 酸度系数(pKa) | 15.53±0.46(Predicted) |
| 外观 | Off-white to light yellow Solid |
| InChI | InChI=1S/C16H21FN4O3/c1-11(22)19-9-13-10-21(16(23)24-13)12-2-3-15(14(17)8-12)20-6-4-18-5-7-20/h2-3,8,13,18H,4-7,9-10H2,1H3,(H,19,22)/t13-/m0/s1 |
| InChIKey | DSRPYQXHWUDRBP-ZDUSSCGKSA-N |
| SMILES | C(NC[C@@H]1OC(=O)N(C2=CC=C(N3CCNCC3)C(F)=C2)C1)(=O)C |
安全数据
| 危险性符号(GHS) | ![]() GHS07 |
| 警示词 | 警告 |
| 危险性描述 | H302-H315-H319-H335 |
| 防范说明 | P261-P305+P351+P338 |
制备方法
174649-06-0
154590-66-6
以化合物(CAS:174649-06-0)为原料合成(S)-N-((3-(3-氟-4-哌嗪-1-基苯基)-2-氧代噁唑烷-5-基)甲基)-乙酰胺的一般步骤如下:将0.4 g(0.85 mmol)的化合物15和0.06 g 10%钯/碳催化剂悬浮于19 mL甲醇和6 mL二氯甲烷的混合溶剂中,在氢气氛围下搅拌反应48小时。反应完成后,将反应混合物通过硅藻土垫过滤以去除催化剂。用50 mL二氯甲烷洗涤滤饼,随后用25 mL乙酸乙酯洗涤。合并滤液并浓缩,得到灰白色固体产物。将该固体产物用50 mL 10%甲醇-乙酸乙酯混合溶剂在温水浴中研磨30分钟,随后冷却至0℃以促进结晶。过滤收集结晶,得到化合物16,为白色固体。产率为91%;熔点为198-200℃;IR(KBr)υmax:3436和3329(NH),1741(C=O)和1644(CONH)cm-1;1H NMR(DMSO-d6)δ:9.03(br s,2H,NH2+),8.26(t,1H,J=6 Hz,CONH),7.50(dd,1H,J=15和2.5 Hz,H2氟苯),7.19(dd,1H,J=9和2.5 Hz,H6氟苯),7.12(t,1H,J=9 Hz,H5氟苯),4.71-4.68(m,1H,H5恶唑烷酮),4.07(t,1H,J=9 Hz,CH2NH),3.69(dd,1H,J=9和6 Hz,CH2NH),3.39(t,2H,J=6 Hz,H4恶唑烷酮),3.22-3.21(m,4H,哌嗪),3.17-3.16(m,4H,哌嗪),1.81(s,3H,CH3CO);MS:m/z 337(45,M+),295(100),250(53),191(32),57(32);元素分析计算值(C17H24ClFN4O3):C,52.78;H,6.25;Cl,9.16;F,4.91;N,14.48。实测值:C,52.94;H,6.10;Cl,9.24;F,4.73;N,14.60。
参考文献:
[1] Tetrahedron Letters, 2006, vol. 47, # 38, p. 6799 - 6802
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 65 - 70
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 3, p. 893 - 900
[4] Patent: WO2011/37731, 2011, A1. Location in patent: Page/Page column 118-119
[5] Tetrahedron Letters, 1996, vol. 37, # 44, p. 7937 - 7940
