Ethanol → 3-(2-ethoxypropan-2-yl)-1-phenyl-1H-pyrazol-5-amine

HRID 871535Notes

Reaction equation

F[C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[C:11]1([NH:17][NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:19][CH2:20][OH:21]>>[CH2:20]([O:21][C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:18]=1)([CH3:9])[CH3:8])[CH3:19]

Participants

Reactant 3

HCID 702Ethanol

HCID 60962Phenylhydrazine hydrochloride

HCID 866535074-Fluoro-4-methyl-3-oxopentanenitrile

Product 1

HCID 668765183-(2-ethoxypropan-2-yl)-1-phenyl-1H-pyrazol-5-amineYield 24%

Procedure

Using the procedure described in Example 161B Step 2, using 4-fluoro-4-methyl-3-oxopentanenitrile (0.77 g, 6 mmol) and phenylhydrazine hydrochloride (0.954 g, 6.6 mmol) in EtOH at 95° C. for 3 hours, which was purified by silica gel chromatography with 10-35% EtOAc/hexane to afford 3-(2-ethoxypropan-2-yl)-1-phenyl-1H-pyrazol-5-amine as solid (0.315 g, 24%). 1H NMR (300 MHz, CDCl3) δ 7.54 (m, 2H), 7.43 (m, 2H), 7.27 (m, 1H), 5.60 (s, 1H), 3.83 (br, 2H), 3.35 (q, 2H), 1.63 (s, 6H), 1.15 (t, 3H); LC-MS (ESI) m/z 246 (M+H)+.

Workup

customat 95° C.
customfor 3 hours
customwhich was purified by silica gel chromatography with 10-35% EtOAc/hexane

Sources & evidence

ORD record: ord-9ac8f75ebebe4d22a346cf0c6ec33c57
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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