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

HRID 1096153
Notes
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Reaction equation

HRID 1096153 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 a 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 afford 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-24dd8a4b438c42db90995cbdebd29f8a
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138217B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes