N-bromobutanimide → HCID 57070594, compound

HRID 2227208Notes

Reaction equation

HRID 2227208 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]([C@@H:9]3[O:14][C@H:13]([CH3:15])[C@@:11]([C:16](=[O:18])[CH3:17])([OH:12])[C@H:10]3[F:19])[CH:7]=[N:8][C:4]=2[CH:3]=1.C1C(=O)N([Br:30])C(=O)C1>C1(C)C=CC=CC=1>[Br:30][C:7]1[N:6]([C@@H:9]2[O:14][C@H:13]([CH3:15])[C@@:11]([C:16](=[O:18])[CH3:17])([OH:12])[C@H:10]2[F:19])[C:5]2[CH:20]=[C:21]([Cl:22])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57170925HCID 57170925, compound

Product 1

HCID 57070594HCID 57070594, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

5,6-Dichloro-1-(3-acetyl-2,5-dideoxy-2-fluoro-beta-D-ribofuranosyl)-1H-benzimidazole (0.45 g, 1.3 mmoles) was boiled in toluene to remove water. Excess toluene was removed in vacuo. THF (Aldrich, Sure Seal, 20 mL) was added and the solution heated to reflux in an 85° C. oil bath. NBS (Aldrich, 0.46 g, 2.6 mmoles, 2 eq.) was added and the reaction refluxed 7 mins. A second portion (0.23 g, 1.3 mmoles, 1 eq.) was added and reflux continued 10 mins. The reaction was removed from the heat, diluted with chloroform (40 mL) and cooled to room temperature. The solution was washed with sat. sodium bicarbonate (2×), dried with MgSO4 and filtered. The solvents were removed in vacuo and the residue purified by chromatography on 75 g of silica gel eluted with ethyl acetate/hexane (1:4, v/v). The product containing fractions were combined and the solvents removed in vacuo. The yield was 0.42 g, 75%. MS (FAB+): m/z, 425; 1H NMR (DMSO-d6) δ7.99 (s,1H, Ar—H), 7.97 (s, 1H, Ar—H), 6.27 (d, 1H, H-1′, J=19 Hz), 5.69 (d, 1H, H-2′, J=53 Hz), 5.1 (m, 1H), 4.25 (m, 1H), 2.13 (s, 3H, acetyl), 1.45 (d, 3H, H-5′, J=6 Hz).

Workup

  1. customto remove water
  2. customExcess toluene was removed in vacuo
  3. additionTHF (Aldrich, Sure Seal, 20 mL) was added
  4. temperaturethe solution heated
  5. temperaturethe reaction refluxed 7 mins
  6. additionA second portion (0.23 g, 1.3 mmoles, 1 eq.) was added
  7. temperaturereflux
  8. customThe reaction was removed from the heat
  9. additiondiluted with chloroform (40 mL)
  10. temperaturecooled to room temperature
  11. washThe solution was washed with sat. sodium bicarbonate (2×)
  12. dry with materialdried with MgSO4
  13. filtrationfiltered
  14. customThe solvents were removed in vacuo
  15. customthe residue purified by chromatography on 75 g of silica gel
  16. washeluted with ethyl acetate/hexane (1:4, v/v)
  17. additionThe product containing fractions
  18. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-597b3c2fb540476d9e2d32fe5f95a970
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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