三乙胺 → tert-Butyl 4-((2-bromo-4-fluorophenyl)carbamoyl)piperidine-1-carboxylate

HRID 1441663

反应方程式

HRID 1441663 反应方程式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[Br:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[NH2:29].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:29][C:23]2[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=2[Br:21])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参与物

8

反应物 4

HCID 8471三乙胺HCID 24386氯化亚砜HCID 2428732-溴-4-氟苯胺HCID 3928711-Boc-4-哌啶甲酸

产物 1

HCID 58878481tert-Butyl 4-((2-bromo-4-fluorophenyl)carbamoyl)piperidine-1-carboxylate

试剂、催化剂与溶剂 3

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 1049吡啶溶剂HCID 6344二氯甲烷溶剂2 次

实验过程

Piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (16.5 g, 72.00 mmol) was dissolved in dry methylene chloride (100 mL) and dry pyridine (15 mL). To the reaction mixture was then added thionyl chloride (10.28 g, 86.40 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was then added successively, under nitrogen atmosphere, 2-bromo-4-fluoro-phenylamine (15.0 g, 79.00 mmol), dry triethylamine (25.50 g, 252.0 mmol), dry methylene chloride (120 mL), 4-(dimethylamino)pyridine (0.87 g, 7.20 mmol) and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was then partitioned with aqueous 2N HCl and tert-butyl methyl ether. The organic layer was washed with aqueous 2N HCl, aqueous NaHCO3, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a solid.

后处理

  1. additionTo the reaction mixture was then added successively, under nitrogen atmosphere
  2. customThe reaction mixture was then partitioned with aqueous 2N HCl and tert-butyl methyl ether
  3. washThe organic layer was washed with aqueous 2N HCl, aqueous NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

来源与证据

ORD记录
ord-8e2005afd5824055b07c184c86d6bd04
来源数据集
uspto-grants-2010_02
专利号
US07655670B2

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