Hydrochloric Acid → HCID 1382089, compound

HRID 1889028Notes

Reaction equation

HRID 1889028 reaction equation
C(OC([NH:8][NH:9][C:10]([C:12]1[CH:16]=[N:15][S:14][N:13]=1)=[O:11])=O)(C)(C)C.Cl.O1CCOCC1>>[S:14]1[N:15]=[CH:16][C:12]([C:10]([NH:9][NH2:8])=[O:11])=[N:13]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66599184HCID 66599184, compound

Product 1

HCID 1382089HCID 1382089, compound

Procedure

Solid t-butyl-2-(1,2,5-thiadiazol-3-ylcarbonyl)hydrazinecarboxylate (I86) (265 mg, 0.890 mmol) was treated with a solution of hydrochloric acid (4 M) in dioxane (4.45 ml, 17.79 mmol) and stirred under argon at RT for 6 hr. The solvent was evaporated in vacuo and the residue dissolved in methanol (˜10 ml), added to a 10 g SCX column and eluted with Dichloromethane (˜50 ml), methanol (˜50 ml) and a solution of ammonia (2 M) in methanol (˜100 ml). The basic fractions were combined and evaporated in vacuo to afford the free base as a white solid in 95.5 mg.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in methanol (˜10 ml)
  3. additionadded to a 10 g SCX column
  4. washeluted with Dichloromethane (˜50 ml), methanol (˜50 ml)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-59751807884748ac92b74d3b92db4006
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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