Hydrazine hydrate (1:1) → 3,5-diamino-N-(2-methyl-3-phenyl-imidazol-4-yl)-1H-pyrazole-4-carboxamide

HRID 1850694Notes

Reaction equation

[NH2:1][C:2](C(Cl)(Cl)Cl)=[C:3]([C:19]#[N:20])[C:4]([NH:6][C:7]1[N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([CH3:12])=[N:10][CH:11]=1)=O.[OH2:25].[NH2:26][NH2:27]>CN1C(=O)CCC1>[NH2:20][C:19]1[C:3]([C:4]([NH:6][C:7]2[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]([CH3:12])=[N:10][CH:11]=2)=[O:25])=[C:2]([NH2:1])[NH:27][N:26]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 3-amino-4,4,4-trichloro-2-cyano-N-(2-methyl-3-phenyl-imidazol-4-yl)but-2-enamide (150 mg, 0.39 mmol) in NMP (1.5 mL) was added hydrazine hydrate (0.032 mL, 1.02 mmol) and the mixture heated to 85° C. for 3 h. The reaction was allowed to cool to RT and concentrated in vacuo to give 3,5-diamino-N-(2-methyl-1-phenyl-1H-imidazol-5-yl)-1H-pyrazole-4-carboxamide as an orange oil. (116 mg, 100%). MS (ES+) 298.2.

Workup

temperatureto cool to RT
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4d692126d2e9427fbd21bad5530ac24d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957078B2

Reaction notes

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