HCID 10646980, compound → HCID 516036, compound

HRID 1900120Notes

Reaction equation

HRID 1900120 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]=[C:26]([Cl:29])[CH:27]=[CH:28][C:4]=2[N:3]=1>N>[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]=[C:26]([Cl:29])[CH:27]=[CH:28][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 10646980HCID 10646980, compound

Product 1

HCID 516036HCID 516036, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

2,6-Dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole (66) (1.8 grams) was dissolved in methanolic ammonia (35 ml). The reaction material was stirred in a pressure bottle for 5 hours at room temperature. Volatile materials were evaporated in vacuo to provide a white powdery precipitate. This residue was recrystallized from MeOH to yield 561 mg (2 crops, 85%) of 67 as colorless needles. MP 162°-163° C. 1H NMR (DMSO-d6): d 8.30 (d, 1, 7-H, J7-5 =2.0 Hz), 7.64 (d, 1, 4-H, J4-5 =8.5 Hz), 7.31 (dd, 1, 5-H), 5.89 (d, 1, 1'-H, J1'-2' =8.0 Hz), 5.49 (d, 1, 2'-OH, J2'-2' =6 5 Hz), 5.35 (t, 1, 5'-OH, J5'-5'OH =5.0 Hz), 5.28 (d, 1,3'-OH, J3'-3'OH=4.5 Hz), 4.46 (m, 1, 2'-H, J2'-3' =5.5 Hz), 4.14 (m, 1, 3'-H, J3'-4' =2.0 Hz), 4.00 (m, 1,4'-H, J4'-5' =J4'-5' =3.0 Hz), 3.70 (m, 2, 5'-H and 5"-H, J5'-5" =12.0 Hz). 13C NMR (DMSO-d6) d 140.72 (C2), 140.17 (C3a), 133.56 (C7a), 127.86 (C6), 123.23 (C5), 128.34 (C6), 120.03 (C4), 113.15 (C7), 89.00 (C1'), 86.26 (C4'), 71.37 (C2'), 69.72 (C3'), 61.12 (C5').

Workup

  1. customVolatile materials were evaporated in vacuo
  2. customto provide a white powdery precipitate
  3. customThis residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-2d317027b1b74e64b911be050ae7e9d8
Source dataset
uspto-grants-1996_11
Patent number
US05574058

Reaction notes

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