Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

HRID 631725Notes

Reaction equation

HRID 631725 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>>[C:13]([C:14]1[CH:15]=[C:16]([NH2:17])[N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[N:11]=1)([CH3:20])([CH3:19])[CH3:12]

Participants

3

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 111393953-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amineYield 63%

Procedure

The title compound was prepared from 4-methoxyphenylhydrazine hydrochloride (1.39 g, 8.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.0 g, 8.0 mmol) using the procedure in Example 161A Step 3 to give 3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine (1.24 g, 4.08 mmol, 63%). 1H NMR (300 MHz, DMSO-d6) δ 7.42 (d, 2H), 7.00 (d, 2H), 5.33 (s, 1H), 5.05 (s, 2H), 1.20 (s, 9H); LC-MS (ESI) m/z 246 (M+H)+.

Sources & evidence

ORD record
ord-1b10d010e41e4d4eaee6c3082dcf2bba
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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