2-[3-(4-Benzyloxybutylamino)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole → 2-[3-(4-Hydroxybutylamino)benzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985850Notes

Reaction equation

C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:15]=[C:16]([CH:37]=[CH:38][CH:39]=1)[CH2:17][NH:18][C:19]1[N:23]([C@@H:24]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]2[OH:26])[C:22]2[CH:33]=[CH:34][CH:35]=[CH:36][C:21]=2[N:20]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:15]=[C:16]([CH:37]=[CH:38][CH:39]=1)[CH2:17][NH:18][C:19]1[N:23]([C@@H:24]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]2[OH:26])[C:22]2[CH:33]=[CH:34][CH:35]=[CH:36][C:21]=2[N:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-[3-(4-Benzyloxybutylamino)benzylamino]-1-(β-D-ribofuranosyl)-1H-benzimidazole (44 mg) was dissolved in ethanol (5 mL). To the solution was added a catalytic amount of 10% palladium-carbon powder, and the mixture was stirred at 60° C. under a hydrogen atmosphere for 24 hour. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (22 mg).

Workup

customThe insoluble material was removed by filtration
customthe solvent of the filtrate was removed under reduced pressure

Sources & evidence

ORD record: ord-300c166caf65461da0782d9fd530ee04
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547680B2

Reaction notes

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