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

HRID 506443Notes

Reaction equation

HRID 506443 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-9feba11d7ae146a1b7d1c8296c3b321f
Source dataset
uspto-grants-2010_08
Patent number
US07786048B2

Reaction notes

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