Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-tert-Butyl-1-(2-fluorophenyl)-1H-pyrazol-5-amine

HRID 871774Notes

Reaction equation

HRID 871774 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16]>>[C:12]([C:13]1[CH:14]=[C:15]([NH2:16])[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[F:2])[N:10]=1)([CH3:19])([CH3:18])[CH3:11]

Participants

3

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)

Product 1

HCID 27611873-tert-Butyl-1-(2-fluorophenyl)-1H-pyrazol-5-amineYield 66%

Procedure

using the procedure in Example 161A Step 3, 2-fluorophenylhydrazine hydrochloride (1.30 g, 8.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.0 g, 8.0 mmol) were reacted to give 3-tert-butyl-1-(2-fluorophenyl)-1H-pyrazol-5-amine (1.23 g, 5.28 mmol, 66%). 1H NMR (300 MHz, DMSO-d6) δ 7.46-7.29 (m, 4H), 5.31 (s, 1H), 5.05 (br s, 2H), 1.20 (s, 9H); LC-MS (ESI) m/z 234 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d6aaff00a59d42b98d7ec79e71513990
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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