醋酸 → N-(4-aminobenzyl)amino-1H-benzimidazole

HRID 19518

反应方程式

HRID 19518 反应方程式
[N+:1]([C:4]1[CH:11]=[CH:10][C:7](C=O)=[CH:6][CH:5]=1)([O-])=O.[C:12](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH2:30][C:31]1[CH:39]=[C:38]2[C:34]([CH:35]=[N:36][NH:37]2)=[CH:33][CH:32]=1>ClCCl>[NH2:30][C:31]1[CH:39]=[CH:38][C:34]([CH2:35][NH:36][N:37]2[C:5]3[CH:6]=[CH:7][CH:10]=[CH:11][C:4]=3[N:1]=[CH:12]2)=[CH:33][CH:32]=1

参与物

6

反应物 4

HCID 176醋酸HCID 541对硝基苯甲醛HCID 814232H-indazol-6-amineHCID 5049666三乙酰氧基硼氢化钠

产物 1

HCID 17864618N-(4-aminobenzyl)amino-1H-benzimidazole收率 86%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

To the solution of 0.145 g (0.98 mmol) of 4-nitrobenzaldehyde in 3 ml of dichloromethane was added 0.31 g (1.47 mmol) of sodium triacetoxyborohydride, 0.6 ml (0.98 mmol) of acetic acid and 0.13 g (0.98 mmol) of 6-aminoindazole. After stirring the mixture overnight at room temperature, the solvent was evaporated. The resulting residue was dissolved in 10 ml of ethanol, 20 mg of 10% palladium on carbon was added and stirred under hydrogen atmosphere overnight. The catalyst was filtered off through celite. After evaporation of the solvent the residue was purified by HPLC and lyophilized to yield 0.2 g (86%) of the title compound. 1H-NMR (CDCl3) δ: 4.12 (2H, br), 6.50-6.70 (5H, m), 7.52 (1H, d), 7.86-7.94 (2H, m), 8.18 (1H, br), 8.29 (1H, br).

后处理

  1. customthe solvent was evaporated
  2. dissolutionThe resulting residue was dissolved in 10 ml of ethanol
  3. addition20 mg of 10% palladium on carbon was added
  4. stirringstirred under hydrogen atmosphere overnight
  5. filtrationThe catalyst was filtered off through celite
  6. customAfter evaporation of the solvent the residue
  7. customwas purified by HPLC

来源与证据

ORD记录
ord-e3caf4afabd54e539ab301437c037bbb
来源数据集
uspto-grants-2010_06
专利号
US07745443B2

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