Hydrochloric Acid → tert-butyl 3-amino-1H-thieno[2,3-c]pyrazole-5-carboxylate

HRID 908891Notes

Reaction equation

HRID 908891 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:6][C:7]=1[NH:8][NH2:9])#[N:2].Cl>CO.C(OCC)(=O)C>[NH2:2][C:1]1[C:3]2[CH:4]=[C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:6][C:7]=2[NH:8][N:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11622817Tert-butyl 4-cyano-5-hydrazinothiophene-2-carboxylate

Product 1

HCID 178450636tert-butyl 3-amino-1H-thieno[2,3-c]pyrazole-5-carboxylateYield 89.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-cyano-5-hydrazinothiophene-2-carboxylate (1.0 g, 4.2 mmol) and hydrochloric acid (0.7 mL of 37% solution) in methyl alcohol (15 mL) was stirred at room temperature for 14 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with an aqueous solution of sodium bicarbonate. Organic layer was separated, dried over anhydrous sodium sulfate, and evaporated to give 0.9 g of the title compound.

Workup

  1. washwashed with an aqueous solution of sodium bicarbonate
  2. customOrganic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-fad4e1ba06d540e5b42d7e4cceb87736
Source dataset
uspto-grants-2011_09
Patent number
US08017643B2

Reaction notes

Loading…