Water → 2-[3-(3-Chloropropoxy)-4-ethoxybenzylamino]-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985836Notes

Reaction equation

HRID 1985836 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]2[O:9][C:10](=[O:12])[CH3:11])[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1.[Cl:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[O:42][CH2:43][CH3:44])[CH:37]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>O1CCCC1>[Cl:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[O:42][CH2:43][CH3:44])[CH2:37][NH:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]2[O:9][C:10](=[O:12])[CH3:11])[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 231438703-(3-Chloropropoxy)-4-ethoxybenzaldehydeHCID 688410382-Amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 577201682-[3-(3-Chloropropoxy)-4-ethoxybenzylamino]-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazoleYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

2-Amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-benzimidazole (13.7 g) and 3-(3-chloropropoxy)-4-ethoxybenzaldehyde (15.3 g) were suspended in tetrahydrofuran (150 mL), and the mixture was stirred at 70° C. for 20 hours. To the stirred reaction mixture was added sodium triacetoxyborohydride (21.7 g) under ice-cooling, and the mixture was stirred at room temperature for 24 hours. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/3) to give the title compound (16.8 g).

Workup

  1. customTo the stirred reaction mixture
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 24 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-9f1332b37f1849e988554916079990e2
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

Loading…