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【结 构 式】

【分子编号】40036

【品名】tert-butyl 4-[5-(2-chloro-4-pyridinyl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C24H26ClFN4O2

【 分 子 量 】456.9473032

【元素组成】C 63.08% H 5.74% Cl 7.76% F 4.16% N 12.26% O 7%

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:(VII)

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
Extended Information