Hydrazine hydrate (1:1) → 5-amino-3-((4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-1H-pyrazole-4-carboxamide
Reaction equation
C([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=O)#N.Cl[C:13]1[CH:14]=[C:15]([NH:19][C:20]2[C:24]([C:25]([NH2:27])=[O:26])=[C:23]([NH:28]CC3C=CC(O)=CC=3)[NH:22][N:21]=2)[CH:16]=[CH:17][CH:18]=1.[NH2:37][C:38]1C=CC(C2CCCCN2C2CCNCC2)=CC=1.O.NN>CCO>[NH2:28][C:23]1[NH:22][N:21]=[C:20]([NH:19][C:15]2[CH:14]=[CH:13][C:18]([N:6]3[CH:4]=[C:3]([CH3:7])[N:37]=[CH:38]3)=[CH:17][CH:16]=2)[C:24]=1[C:25]([NH2:27])=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Dissolved 0.500 g 2-cyano-3,3-bis(methylthio)acrylamide in 15 mL EtOH and added 4-methyl-1′-[(4-aminophenyl)1,4′-bipiperidine (1.0 eq.). Stirred reaction at 75° C. until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75° C. until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-1H-pyrazole-4-carboxamide as a yellow powder. Product was allowed to dry under vacuum for 1 hr.
Workup
- customreaction at 75° C.
- customOnce complete (18 hrs), reaction
- customwas brought to room temperature
- filtrationfiltered
- customto obtain a light yellow powder as product
- customto dry under vacuum for 1 hr
- customReaction
- custom(18 hrs), reaction
- customwas brought to room temperature
- filtrationfiltered
Sources & evidence
- ORD record
- ord-e6599a458b68426a97a41a4c88f4a2de
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346792B2
Reaction notes
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