Hydrazine hydrate (1:1) → 5-amino-3-((4-(methylsulfonyl)benzyl)amino)-1H-pyrazole-4-carboxamide
Reaction equation
[C:1]([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=[O:5])#[N:2].[CH3:12][S:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1)(=[O:15])=[O:14].O.[NH2:25][NH2:26]>CCO>[NH2:2][C:1]1[NH:26][N:25]=[C:7]([NH:21][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([S:13]([CH3:12])(=[O:14])=[O:15])=[CH:17][CH:18]=2)[C:3]=1[C:4]([NH2:6])=[O:5]Participants
Conditions
- Temperature
- 75 °C
Procedure
Dissolved 0.500 g 2-cyano-3,3-bis(methylthio)acrylamide in 15 mL EtOH and added 4-Methylsulphonylbenzylamine (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-(methylsulfonyl)benzyl)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-1b599d1dd5a243f58c1186066cf1d154
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346792B2
Reaction notes
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