Trimethylsilyl triflate → HCID 53700596, compound

HRID 2227218Notes

Reaction equation

HRID 2227218 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([Cl:11])[NH:7][C:6]=2[CH:5]=[C:4]([Cl:12])[C:3]=1[Cl:13].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.C(O[CH:30]1[O:42][C@H:41]([CH3:43])[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:31]1[O:32][C:33](=[O:35])[CH3:34])(=O)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([Cl:11])[N:7]([C@@H:30]3[O:42][C@H:41]([CH3:43])[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:31]3[O:32][C:33](=[O:35])[CH3:34])[C:6]=2[CH:5]=[C:4]([Cl:12])[C:3]=1[Cl:13]

Participants

7

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 11196237Tri-O-acetyl-5-deoxy-D-ribofuranoseHCID 18472159HCID 18472159, compound

Product 1

HCID 53700596HCID 53700596, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 4-bromo-2,5,6-trichloro-1H-benzimidazole (0.30 g, 1 mmol), in acetonitrile (5 mL) was added N,O-bis(trimethylsilyl)acetamide (0.25 mL, 1 mmol). The resulting mixture was allowed to stir at 65° C. for 15 min., followed by the addition of 1,2,3-tri-O-acetyl-5-deoxyribofuranose (0.31 g, 1.2 mmol) in acetonitrile (5 mL) and trimethylsilyltrifluoromethane sulfonate (0.25 mL, 1.3 mmol). The mixture was allowed to stir at 65° C. for 20 min and was then allowed to cool to RT. The mixture was diluted with ethyl acetate and was washed with a saturated NaHCO3/NaCl solution, dried over MgSO4 and the solvents were removed by rotary evaporation. The product was purified by flash chromatography using chloroform as eluent followed by recrystallization from methanol to provide 0.28 g (55%) of the title compound as white crystals; m.p. 138-141° C.; 1H NMR (DMSO-d6) δ: 8.18 (s, 1H), 6.19 (d, 1H), 5.61 (dd, 1H), 5.25 (dd, 1H), 4.24 (m, 1H), 2.14 (s, 3H), 2.02 (s, 3H), 1.50 (d, 3H).

Workup

  1. stirringto stir at 65° C. for 20 min
  2. temperatureto cool to RT
  3. washwas washed with a saturated NaHCO3/NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvents were removed by rotary evaporation
  6. customThe product was purified by flash chromatography
  7. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-62129636baaf43248e9cfa8bf5b031cc
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

Loading…