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

HRID 448127
Notes
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Reaction equation

HRID 448127 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-29d1742330254ea8b4adefd037829f1b
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481584B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes