Hydrazine hydrate (1:1) → 4-(3-amino-1H-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 1038381Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:10]2[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:12]([CH3:19])=[C:11]2[C:20]#[N:21])[CH:6]=[CH:7][C:8]=1F)#[N:2].O.[NH2:23][NH2:24]>C(O)CCC>[NH2:2][C:1]1[C:3]2[C:8](=[CH:7][CH:6]=[C:5]([CH:10]3[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:12]([CH3:19])=[C:11]3[C:20]#[N:21])[CH:4]=2)[NH:24][N:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 9.5 g (34.1 mmol) 4-(3-cyano-4-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile (Example 1A) and 10 g (312 mmol) hydrazine hydrate in n-butyl alcohol (75 ml) was stirred at 80° C. for 5 h. The mixture was cooled and concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound (5.6 g, 57% of th.) as a pale yellow solid.

Workup

temperatureThe mixture was cooled
concentrationconcentrated under reduced pressure
additionSaturated aqueous sodium bicarbonate solution was added to the residue
extractionthe mixture was extracted with ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3185e72676fb4218b791f1bcd06e6178
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551989B2

Reaction notes

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