Acetic Acid → N-(4-aminobenzyl)amino-1H-benzimidazole

HRID 1767703

反応式

HRID 1767703 の反応式
[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

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 814231H-Indazol-6-amineHCID 5049666Sodium triacetoxyborohydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2d14a5c4c0d14dc98dad03a016968b92
出典データセット
uspto-grants-2007_06
特許番号
US07235558B2

関連ノート

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