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 965395Notes

Reaction equation

HRID 965395 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-c7abe02af26848919b16975ea42bad8b
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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