Piperidine → N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitro-5-(piperidin-1-yl)benzamide

HRID 926859Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:24]([O-:26])=[O:25])=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=2)[N:11]=1)=[O:8].C(=O)([O-])[O-].[K+].[K+].[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>CN(C)C=O>[CH3:22][C:17]1[CH:16]=[C:15]([N:12]2[CH:13]=[CH:14][C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:23]=[C:2]([N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:3]=[CH:4][C:5]=3[N+:24]([O-:26])=[O:25])=[N:11]2)[CH:20]=[CH:19][C:18]=1[CH3:21]

Participants

Conditions

Temperature: 110 °C

Procedure

Into a 50-mL round bottom flask, was placed a solution of 5-chloro-N-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-yl)-2-nitrobenzamide 4g (300 mg, 0.81 mmol, 1.00 equiv) in N,N-dimethylformamide (10 mL), potassium carbonate (330 mg, 2.39 mmol, 3.00 equiv), and piperidine (200 mg, 2.35 mmol, 3.00 equiv). The resulting solution was stirred for 4 h at 110° C. The resulting mixture was concentrated under vacuum. The residue was dissolved in 50 mL of ethyl acetate. The resulting mixture was washed with 2×30 mL of brine, dried over sodium sulfate, and concentrated under vacuum. This resulted in 300 mg (88%) of product as a yellow solid.

Workup

customInto a 50-mL round bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
dissolutionThe residue was dissolved in 50 mL of ethyl acetate
washThe resulting mixture was washed with 2×30 mL of brine
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-5d89e52acc284920973eb94a15711d87
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09289430B2

Reaction notes

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