Potassium Carbonate → N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(3,3-dimethylpiperazin-1-yl)benzamide

HRID 1911413Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([NH:18][C:19](=[O:27])[C:20]3[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=3)[NH:16][N:17]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:28][C:29]1([CH3:35])[CH2:34][NH:33][CH2:32][CH2:31][NH:30]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([NH:18][C:19](=[O:27])[C:20]3[CH:25]=[CH:24][C:23]([N:33]4[CH2:32][CH2:31][NH:30][C:29]([CH3:35])([CH3:28])[CH2:34]4)=[CH:22][CH:21]=3)[NH:16][N:17]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-fluorobenzamide (0.1 g, 0.27 mmol) and 2,2-dimethylpiperazine (0.124 g, 1.04 mmol) were stirred at 60° C. for 20 mins. Potassium carbonate (0.033 ml, 0.54 mmol) and DMSO (1 ml) were added and the reaction stirred at 120° C. in a sealed tube for 16 days. The reaction mixture was cooled and evaporated. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (6.00 mg, 2.000%) as a colourless gum.

Workup

temperatureThe reaction mixture was cooled
customevaporated
customThe crude product was purified by preparative HPLC
additionFractions containing the desired compound
customwere evaporated to dryness

Sources & evidence

ORD record: ord-d211aa7aff944a17b6c1405b15990f42
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604022B2

Reaction notes

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