2-[3-(3-Aminopropoxy)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole → HCID 178512990, compound

HRID 1985852Notes

Reaction equation

HRID 1985852 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[CH2:9][NH:10][C:11]1[N:15]([C@@H:16]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]2[OH:18])[C:14]2[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=2[N:12]=1.C(OC([NH:42][C:43](N1C=CC=N1)=[NH:44])=O)C1C=CC=CC=1>O1CCCC1>[NH:1]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[CH2:9][NH:10][C:11]1[N:15]([C@@H:16]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]2[OH:18])[C:14]2[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=2[N:12]=1)[C:43]([NH2:44])=[NH:42]

Participants

4

Reactant 2

HCID 577201972-[3-(3-Aminopropoxy)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazoleHCID 137319688N-(Carbobenzoxy)-1H-pyrazole-1-carboxamidine

Product 1

HCID 178512990HCID 178512990, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2-[3-(3-Aminopropoxy)benzylamino]-1-(β-D-ribofuranosyl)-1H-benzimidazole (0.2 g) and N-(benzyloxycarbonyl)-1H-pyrazol-1-carboxamidine (0.55 g) were suspended in tetrahydrofuran (2.5 mL), and the mixture was stirred at 60° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in methanol (4 mL). To the solution was added a catalytic amount of 10% palladium-carbon powder, and the mixture was stirred at 40° C. under a hydrogen atmosphere for 2 hour. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90) to give the title compound (0.01 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in methanol (4 mL)
  3. additionTo the solution was added a catalytic amount of 10% palladium-carbon powder
  4. stirringthe mixture was stirred at 40° C. under a hydrogen atmosphere for 2 hour
  5. customThe insoluble material was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90)

Sources & evidence

ORD record
ord-7d760f2eb749423697cdc90276fcb34e
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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