Hydrazine hydrate (1:1) → 5-amino-3-((4-isopropylphenyl)amino)-1H-pyrazole-4-carboxamide

HRID 527263Notes

Reaction equation

HRID 527263 reaction equation
[C:1]([C:3](=[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=1)SC)[C:4]([NH2:6])=[O:5])#[N:2].O.[NH2:21][NH2:22]>C(O)C>[NH2:2][C:1]1[NH:22][N:21]=[C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867018702-Cyano-3-((4-isopropylphenyl)amino)-3-(methylthio)acrylamide

Product 1

HCID 867018725-amino-3-((4-isopropylphenyl)amino)-1H-pyrazole-4-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-cyano-3-((4-isopropylphenyl)amino)-3-(methylthio)acrylamide (1.360 g) was suspended in 15 mL of ethanol and hydrazine hydrate (360 μL, 1.5 eq.) was added drop wise to the reaction. Reaction was then heated at 75° C. until the starting material was no longer present and confirmed via HPLC. Once starting material was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-isopropylphenyl)amino)-1H-pyrazole-4-carboxamide as an off white to yellow powder. The product was allowed to dry under vacuum for 1 hr (850 mg, 66% yield).

Workup

  1. customwise to the reaction
  2. customReaction
  3. custom(18 hrs), reaction
  4. customwas brought to room temperature
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7f09d68a8a2346db8cbdc5b070dd9b44
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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