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

HRID 965390Notes

Reaction equation

HRID 965390 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 544024704-azidoacetyl-1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5-(dimethylaminomethyleneamino)imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 537945224-aminoacetyl-1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5-(dimethylaminomethyleneamino)imidazoleYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound (23) (52 mg) obtained in item (12) above was dissolved in methanol (6 ml), and the solution was subjected to catalytic reduction by blowing hydrogen therein in the presence of palladium black as catalyst at room temperature for 30 minutes. The resulting reaction solution was filtered and the filtrate was concentrated to give a solid. The solid material thus obtained was washed with ethyl acetate to yield the titled compound (24) (43 mg) as an insoluble substance. Yield: 89%.

Workup

  1. customThe resulting reaction solution
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customto give a solid
  5. customThe solid material thus obtained
  6. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-e022ecd8619b4675bb9d35c2b2376efe
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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