4-azidoacetyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-(dimethylaminomethyleneamino)imidazole → 4-aminoacetyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-(dimethylaminomethyleneamino)imidazole

HRID 1419488Notes

Reaction equation

HRID 1419488 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([C@@H:17]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@@H:18]2[F:25])[C:11]=1[N:12]=[CH:13][N:14]([CH3:16])[CH3:15])=[O:6])=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][CH2:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([C@@H:17]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@@H:18]2[F:25])[C:11]=1[N:12]=[CH:13][N:14]([CH3:16])[CH3:15])=[O:6]

Participants

5

Reactant 2

HCID 544024694-azidoacetyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-(dimethylaminomethyleneamino)imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 537945214-aminoacetyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-(dimethylaminomethyleneamino)imidazoleYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound (40) (35 mg) obtained in item (7) above was dissolved in methanol (3.5 ml) and the resulting solution was subjected to catalytical reduction by blowing hydrogen therein in the presence of palladium black as catalyst at room temperature for 30 minutes. The reaction solution was filtered and the filtrate was concentrated. The resulting solid was washed with ethyl acetate to yield the titled compound (41) (29.7 mg) as an insoluble solid. Yield: 92%.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated
  3. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-8aaced152d2d443992eb54a7f23056cb
Source dataset
uspto-grants-1999_03
Patent number
US05886167

Reaction notes

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