4-Methyl-3-oxopentanenitrile → 3-isopropyl-1-(pyridin-3-yl)-1H-pyrazol-5-amine

HRID 871750Notes

Reaction equation

HRID 871750 reaction equation
[CH3:1][CH:2]([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[NH:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[NH2:11]>CCO>[CH:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:11]=1)([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 101299214-Methyl-3-oxopentanenitrileHCID 231434543-Hydrazinylpyridine hydrochloride

Product 1

HCID 668772093-isopropyl-1-(pyridin-3-yl)-1H-pyrazol-5-amineYield 32.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Using the procedure described in Example 308A Step 1, to a solution of 4-methyl-3-oxopentanenitrile (303 mg, 2.7 mmol) prepared as described in Example 122A Step 1, in anhydrous EtOH (13 ml) was added 3-hydrazinylpyridine hydrochloride (450 mg, 3.1 mmol) and the reaction mixture was heated at 80° C. overnight to afford 3-isopropyl-1-(pyridin-3-yl)-1H-pyrazol-5-amine (179 mg, 28%) as a solid. 1H NMR (300 MHz, CDCl3) δ 1.25 (d, J=7 Hz, 6H), 2.90-2.99 (m, 1H), 3.93 (brs, 2H), 5.50 (s, 1H), 7.36-7.38 (m, 1H), 7.96 (d, J=8 Hz, 1H), 8.49 (d, J=7 Hz, 1H), 8.67 (s, 1H); LC-MS (ESI) m/z 203 (M+H)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-9a5888fb7cfb4278bc3bbb1e2f36d3e8
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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