Acetic Acid → 2-[4-(1H-Imidazol-1-yl)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985838노트

반응식

HRID 1985838 반응식
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1.[N:29]1([C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)[CH:33]=[CH:32][N:31]=[CH:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.O>[N:29]1([C:34]2[CH:41]=[CH:40][C:37]([CH2:38][NH:1][C:2]3[N:6]([C@@H:7]4[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]4[OH:9])[C:5]4[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=4[N:3]=3)=[CH:36][CH:35]=2)[CH:33]=[CH:32][N:31]=[CH:30]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 688410382-Amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole

생성물 1

HCID 577202912-[4-(1H-Imidazol-1-yl)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole수율 66.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

2-Amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-benzimidazole (94 mg) and 4-(1H-imidazol-1-yl)benzaldehyde (41 mg) were suspended in tetrahydrofuran (3 mL), and the mixture stirred at room temperature for 2 hours. To the reaction mixture was added acetic acid (200 μL), and then was added sodium triacetoxyborohydride (56 mg). The mixture was stirred at room temperature for 24 hours. After adding water to the reaction mixture, and the mixture was concentrated under reduced pressure. The obtained residue was dissolved in ethanol (2 mL). To the mixture was added 5 mol/L aqueous sodium hydroxide solution (0.5 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added acetic acid (1 mL), and the mixture was concentrated under reduced pressure. The obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90) to give the title compound (67 mg).

후처리

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in ethanol (2 mL)
  4. additionTo the mixture was added 5 mol/L aqueous sodium hydroxide solution (0.5 mL)
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. additionTo the reaction mixture was added acetic acid (1 mL)
  7. concentrationthe mixture was concentrated under reduced pressure
  8. customThe obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90)

출처 및 근거

ORD 기록
ord-6841d596e6b3470790ba218c02d1e2bf
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547680B2

반응 노트

불러오는 중…