3,5-Dimethylpyrazole → N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(3,5-dimethyl-1H-pyrazol-1-yl)nicotinamide

HRID 923116Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.Cl[C:11]1[CH:32]=[CH:31][C:14]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:19]=2)=[O:16])=[CH:13][N:12]=1>CN(C=O)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[C:14]2[CH:31]=[CH:32][C:11]([N:5]3[C:4]([CH3:3])=[CH:8][C:7]([CH3:9])=[N:6]3)=[N:12][CH:13]=2)=[CH:19][C:20]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

Conditions

Temperature: 140 °C

Procedure

21 mg of sodium hydride was added to a solution of 84 mg of 3,5-dimethylpyrazole in 2 mL of DMF. The reaction mixture was stirred for 10 min, and then added 100 mg of 6-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)nicotinamide. The reaction was heated to 140° C. for 16 h. The mixture was quenched with MeOH and evaporated. The product was purified on reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(3,5-dimethyl-1H-pyrazol-1-yl)nicotinamide. MS (Q1) 404.3 (M)+.

Workup

customThe mixture was quenched with MeOH
customevaporated
customThe product was purified on reverse phase HPLC

Sources & evidence

ORD record: ord-d7c1d82d9d3845bfb5758b46f56ada68
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278961B2

Reaction notes

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