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

HRID 1983079Notes

Reaction equation

HRID 1983079 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 evapored 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

Sources & evidence

ORD record
ord-200d660d2de043d2a3b0be9ec747bc30
Source dataset
uspto-grants-2009_06
Patent number
US07541378B2

Reaction notes

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