乙酸乙酯 → Methyl 2-benzylamino-6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)nicotinate

HRID 340443

反应方程式

HRID 340443 反应方程式
C(N([CH:7]([CH3:9])[CH3:8])CC)(C)C.[C@@H:10]1([NH2:17])[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH2:16].[CH3:18]N1CCCC1=O.[CH2:25]([NH:32][C:33]1[N:42]=[C:41](Cl)[CH:40]=[CH:39][C:34]=1[C:35]([O:37][CH3:38])=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:44]([O:47]CC)(=[O:46])C>O>[CH2:25]([NH:32][C:33]1[N:42]=[C:41]([NH:16][C@@H:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C@@H:10]2[NH:17][C:44]([O:47][C:7]([CH3:9])([CH3:18])[CH3:8])=[O:46])[CH:40]=[CH:39][C:34]=1[C:35]([O:37][CH3:38])=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参与物

7

反应物 5

HCID 8857乙酸乙酯HCID 13387N-甲基吡咯烷酮HCID 81531N,N-二异丙基乙胺HCID 342917顺式-1,2-环己二胺HCID 86683851Methyl 2-benzylamino-6-chloronicotinate

产物 1

HCID 86683850Methyl 2-benzylamino-6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)nicotinate

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

反应条件

温度
120 °C

实验过程

Diisopropylethylamine (7.5 ml) and cis-cyclohexane-1,2-diamine (5.0 g) were added to an N-methylpyrrolidone (50 ml) solution containing methyl 2-benzylamino-6-chloronicotinate (6.0 g), followed by stirring at 120° C. for 11 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and then the solvent was distilled away under reduced pressure. Di-tert-butyl dicarbonate (4.7 g) was added to a tetrahydrofuran (50 ml) solution containing the obtained residue and the resulting mixture was left at rest at room temperature for 3 days. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel:silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=3:1), and a light yellow solid of methyl 2-benzylamino-6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)nicotinate (7.7 g) was thus obtained.

后处理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was collected
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionDi-tert-butyl dicarbonate (4.7 g) was added to a tetrahydrofuran (50 ml) solution
  7. additioncontaining the obtained residue
  8. waitthe resulting mixture was left at rest at room temperature for 3 days
  9. distillationThe solvent was distilled away under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (silica gel:silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=3:1)

来源与证据

ORD记录
ord-efaecba711b74c7a9af3326002b88ba2
来源数据集
uspto-grants-2014_11
专利号
US08895585B2

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