Ammonia → Taribavirin Hydrochloride

HRID 1650875Notes

Reaction equation

HRID 1650875 reaction equation
CO[C:3]([C:5]1[N:9]=[CH:8][N:7]([C@@H:10]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]2[OH:12])[N:6]=1)=[NH:4].[Cl-:19].[NH4+:20].N>CO>[ClH:19].[C@@H:10]1([N:7]2[CH:8]=[N:9][C:5]([C:3]([NH2:4])=[NH:20])=[N:6]2)[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]1[OH:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 129126Methyl 1-ribofuranosyl-1,2,4-triazole-3-carboxamidate

Product 1

HCID 451447Taribavirin HydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The compound (4) residue was dissolved in a minimum amount of methanol (15 mL) and transferred to a pressure bottle. Ammonium chloride (0.61 g, 11.4 mmol) and a solution of methanol saturated at 0° with dry ammonia gas (75 mL) were added, the bottle sealed and the solution stirred at room temperature overnight. The solution was concentrated to dryness in vacuo and the resulting residue crystallized from acetonitrile-ethanol to yield compound (6) as a crystalline solid (2.95 g, 93%). This sample was identical in all respects to an authentic sample prepared as per the above referenced J. T. Witkowski, et al., J. Med. Chem., 1973, 16, 937.

Workup

  1. customthe bottle sealed
  2. concentrationThe solution was concentrated to dryness in vacuo
  3. customthe resulting residue crystallized from acetonitrile-ethanol

Sources & evidence

ORD record
ord-54220757debc4c7fa72e6ba30c8a58b2
Source dataset
uspto-grants-1990_05
Patent number
US04925930

Reaction notes

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