N,N'-羰基二咪唑 → 4-(2-氧代-2,3-二氢-1H-咪唑并[4,5-B]吡啶-1-基)哌啶-1-羧酸叔丁酯

HRID 20069

反应方程式

HRID 20069 反应方程式
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[C:19]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[CH:18][CH:17]=[CH:16][N:15]=1>C(#N)C>[O:2]=[C:1]1[NH:13][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[N:20]1[CH:21]1[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]1

参与物

4

反应物 2

HCID 68263N,N'-羰基二咪唑2 次HCID 222932174-(2-氨基吡啶-3-基氨基)哌啶-1-羧酸叔丁酯

产物 1

HCID 222932204-(2-氧代-2,3-二氢-1H-咪唑并[4,5-B]吡啶-1-基)哌啶-1-羧酸叔丁酯收率 87.1%

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

实验过程

Carbonyldiimidazole (0.70 g, 4.33 mmol) was added to a solution of 2-amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino]pyridine (1.15 g, 3.93 mmol) in acetonitrile (150 mL) at room temperature. After several hours, an additional amount of carbonyldiimidazole was added (0.81 g), and the reaction stirred overnight. The acetonitrile was evaporated in vacuo, the residue partitioned between water and chloroform, and the organic phase washed with saturated brine and dried over magnesium sulfate. The crude product was purified by chromatography (silica gel, 1.2 to 2.5% methanol in methylene chloride gradient elution), which gave the title compound (1.09 g). 1H NMR (500 MHz, CDCl3) δ 9.39 (br s, 1H), 8.04 (dd, J=1, 5 Hz, 1H), 7.33 (dd, J=1, 8 Hz, 1H), 6.99 (dd, J=5, 8 Hz, 1H), 4.50 (m, 1H), 4.32 (br s, 2H), 2.86 (br s, 2H), 2.20 (m, 2H), 1.86 (d, J=12 Hz, 2H), 1.50 (s, 9H).

后处理

  1. waitAfter several hours
  2. customThe acetonitrile was evaporated in vacuo
  3. customthe residue partitioned between water and chloroform
  4. washthe organic phase washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by chromatography (silica gel, 1.2 to 2.5% methanol in methylene chloride gradient elution), which

来源与证据

ORD记录
ord-e2b0cb7991034974b35317f3fc3b60c9
来源数据集
uspto-grants-2010_06
专利号
US07745427B2

关联笔记

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