Triethylamine → 2-(3-Hydroxy-4-phenylbenzylamino)-1-(beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985837Notes

Reaction equation

HRID 1985837 reaction equation
Cl[C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1.[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:24][NH2:25].C(N(CC)CC)C>C(O)C(C)C>[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:24][NH:25][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46942222423-42-3HCID 231438563-Hydroxy-4-phenylbenzylamine

Product 1

HCID 577201662-(3-Hydroxy-4-phenylbenzylamino)-1-(beta-D-ribofuranosyl)-1H-benzimidazoleYield 30.3%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

2-Chloro-1-(β-D-ribofuranosyl)-1H-benzimidazole (0.21 g) and 3-hydroxy-4-phenylbenzylamine (0.19 g) were suspended in isobutanol (5 mL). To the mixture was added triethylamine (0.36 mL), and the mixture was stirred for reflux for 16 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: methanol/ethyl acetate=1/20) to give the title compound (0.1 g).

Workup

  1. temperaturefor reflux for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by column chromatography on silica gel (eluent: methanol/ethyl acetate=1/20)

Sources & evidence

ORD record
ord-f6569efdc7cd4d90a076bf2759357f77
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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