2-Chloro-4,5-dibromo-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole → 2-Chloro-4,5-dibromo-1-beta-D-ribofuranosylbenzimidazole

HRID 6349

Reaction equation

HRID 6349 reaction equation
[Cl: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][C:27]([Br:30])=[C:28]([Br:29])[C:4]=2[N:3]=1>N.CO>[Cl:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[CH:26][C:27]([Br:30])=[C:28]([Br:29])[C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 154800372-Chloro-4,5-dibromo-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole

Product 1

HCID 536732002-Chloro-4,5-dibromo-1-beta-D-ribofuranosylbenzimidazole

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

A solution of 0.529 g (0.930 mmol) of 84 in 25 mL of NH3 /MeOH was stirred in a pressure bottle at room temperature for 5 h. Volatile materials were removed by evaporation and coevaporation with MeOH (3 x, bath temperature<40° C.). The resulting solid was recrystallized from MeOH/H2O to give 0.316 g (2 crops, 77%) of 85 as white crystals. MP: 167°-169° C. MS: (Cl) m/e 440.8837 (20%, MH+ =440.8852). 1H NMR (DMSO-d6): δ8.05 (d, 1, 7-H, J7-6 =8.5 Hz), 7.59 (d, 1, 6-H), 5.89 (d, 1, 1'-H, J1'-2' =7.5 Hz), 5.51 (d, 1, 2'-OH, J2'-2'OH =6.5 Hz), 5.28 (d, 1, 3'-OH, J3'-3'OH =4.5 Hz), 5.27 (t, 1, 5'-OH, J5'-5'OH =5.0 Hz), 4.40 (m, 1, 2'-H, J2'-3' =5.5 Hz), 4.13 (m, 1, 3'-H, J3'-4' =2.0 Hz), 4.00 (m, 1, 4'-H, J4'-5' =J4'-5' =3.5 Hz), 3.68 (m, 2, 5' -H and 5"-H, J5'-5" =12.0 Hz). 13H NMR (DMSO-d6): δ141.70 (C2), 141.58 (C3a), 132.21 (C7a), 127.42 (C6), 118.06 (C5), 114.08 (C4), 113.87 (C7), 89.45 (C1'), 86.34 (C4'), 71.74 (C2'), 69.62 (C3'), 61.07 (C5'). Anal. Calcd. for C12H11Br2ClN2O4 ; C, 32.57; H, 2.51; N, 6.33. Found: C, 32.70; H, 2.33; N, 6.33.

Workup

  1. customVolatile materials were removed by evaporation and coevaporation with MeOH (3 x, bath temperature<40° C.)
  2. customThe resulting solid was recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-6b415f062b484284bdb4a8dfbb581067
Source dataset
uspto-grants-1993_09
Patent number
US05248672

Linked notes

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