|
【结 构 式】 
|
【分子编号】40037 【品名】tert-butyl 4-[5-(2-anilino-4-pyridinyl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C30H32FN5O2 【 分 子 量 】513.6149832 【元素组成】C 70.16% H 6.28% F 3.7% N 13.64% O 6.23% |
合成路线1
该中间体在本合成路线中的序号：(IX)2-Chloronicotinic acid (I) was reduced to alcohol (II) employing borane, generated from NaBH4 and BF3.Et2O. Subsequent oxidation of (II) with N-bromosuccinimide produced aldehyde (III), which was condensed with N-Boc-4-aminopiperidine (IV), yielding imine (V). Addition to (V) of (4-fluorophenyl)-toluenesulfonylmethyl isocyanide (VI) gave rise to imidazole (VII). Then, displacement of the 2-chloro of (VII) by means of aniline (VIII) in the presence of NaH furnished the 2-anilinopyridine derivative (IX). The Boc protecting group of (IX) was finally removed by treatment with trifluoroacetic acid.
| 【1】 Adams, J.L.; Gallagher, T.F.; Sisko, J.; Peng, Z.-Q.; Osifo, I.K.; Boehm, J.C. (SmithKline Beecham plc); Imidazole cpds.. EP 0831830; JP 1999513017; US 5658903; WO 9640143 . |
| 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) | 40032 | 2-chloroisonicotinic acid | 6313-54-8 | C6H4ClNO2 | 详情 | 详情 |
| (II) | 40033 | (2-chloro-4-pyridinyl)methanol | 100704-10-7 | C6H6ClNO | 详情 | 详情 |
| (III) | 29234 | 2-chloroisonicotinaldehyde | C6H4ClNO | 详情 | 详情 | |
| (IV) | 28414 | 4-Amino-1-N-Boc-piperidine; tert-butyl 4-amino-1-piperidinecarboxylate; N-Boc-4-aminopiperidine | 87120-72-7 | C10H20N2O2 | 详情 | 详情 |
| (V) | 40034 | tert-butyl 4-[[(E)-(2-chloro-4-pyridinyl)methylidene]amino]-1-piperidinecarboxylate | C16H22ClN3O2 | 详情 | 详情 | |
| (VI) | 40035 | 2-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]acetonitrile | C15H12FNO2S | 详情 | 详情 | |
| (VII) | 40036 | tert-butyl 4-[5-(2-chloro-4-pyridinyl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-piperidinecarboxylate | C24H26ClFN4O2 | 详情 | 详情 | |
| (VIII) | 12294 | Aniline; Phenylamine | 62-53-3 | C6H7N | 详情 | 详情 |
| (IX) | 40037 | tert-butyl 4-[5-(2-anilino-4-pyridinyl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-piperidinecarboxylate | C30H32FN5O2 | 详情 | 详情 |