Hydrazine hydrate (1:1) → 5-amino-3-((4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-1H-pyrazole-4-carboxamide

HRID 1049220

Reaction equation

[C:1]([C:3](=[C:7](SC)SC)[C:4]([NH2:6])=[O:5])#[N:2].[CH3:12][C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH:17]=1.O.[NH2:26][NH2:27]>CCO>[NH2:2][C:1]1[NH:27][N:26]=[C:7]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([N:16]3[CH:17]=[C:13]([CH3:12])[N:14]=[CH:15]3)=[CH:19][CH:20]=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-methyl-1-(4-aminophenyl)-1H-imidazole (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-e9700085dff04113a156072f1b81ef5e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382237B2

Linked notes

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