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

HRID 1985838Notes

Reaction equation

HRID 1985838 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6841d596e6b3470790ba218c02d1e2bf
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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