Diisopropylethylamine → (+/-)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)-3-(trifluoromethyl)piperazine

HRID 1915876Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][NH:4]1.Cl[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].CCN(C(C)C)C(C)C>CCO>[CH3:17][N:16]1[C:12]([N:7]2[CH2:6][CH2:5][NH:4][CH:3]([C:2]([F:10])([F:9])[F:1])[CH2:8]2)=[C:13]([N+:18]([O-:20])=[O:19])[CH:14]=[N:15]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of (±)-2-(trifluoromethyl)piperazine (1 g, 6.2 mmol), 5-chloro-1-methyl-4-nitro-1H-pyrazole (2.1 g, 13 mmol), DIPEA (2.4 g, 18.6 mmol) in EtOH (10 mL) was heated in a microwave oven at 140° C. for 5 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by silica gel chromatography using DCM/MeOH (10:1) as eluting solvents to afford (±)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)-3-(trifluoromethyl)piperazine as a yellow oil (1.8 g, 99%). MS (ESI) m/z: 280 [M+H+].

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto give a residue
customThe residue was purified by silica gel chromatography
washas eluting solvents

Sources & evidence

ORD record: ord-e223cd396cae4ab9ad0e9e440f69846b
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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