Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-tert-butyl-1-pyridin-4-yl-1H-pyrazol-5-amine

HRID 631692Notes

Reaction equation

HRID 631692 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[NH2:3].[CH3:10][C:11]([CH3:18])([CH3:17])[C:12](=O)[CH2:13][C:14]#[N:15]>>[C:11]([C:12]1[CH:13]=[C:14]([NH2:15])[N:2]([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)[N:3]=1)([CH3:18])([CH3:17])[CH3:10]

Participants

3

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 223202584-Hydrazinylpyridine hydrochloride

Product 1

HCID 109000523-tert-butyl-1-pyridin-4-yl-1H-pyrazol-5-amineYield 17%

Procedure

Following the procedure in Example 161A Step 3, 4-hydrazinopyridine hydrochloride (1.0 g, 6.87 mmol) and 4,4-dimethyl-3-oxopentanenitrile (860 mg, 6.87 mmol) were reacted to give 3-tert-butyl-1-(pyridin-4-yl)-1H-pyrazol-5-amine (250 mg, 1.16 mmol, 17%). 1H NMR (300 MHz, DMSO-d6) δ 8.55 (br s, 2H), 7.69 (br s, 2H), 5.55 (br s, 2H), 5.46 (s, 1H), 1.22 (s, 9H); LC-MS (ESI) m/z 217 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4e81d70f4d46429cbf10fa0ac5d442ba
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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