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

HRID 1767703

반응식

HRID 1767703 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2d14a5c4c0d14dc98dad03a016968b92
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235558B2

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