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

Participants

Role	Name	HCID	Charge
Reactant	3,5-Dimethylpyrazole	HCID 6210	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	6-Chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]pyridine-3-carboxamide	HCID 58614810	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-chloro-3-(pyridin-2-yl)phenyl)-6-(3,5-dimethyl-1H-pyrazol-1-yl)nicotinamide	HCID 58614678	—

Reaction Conditions

Temperature	140 °C

Reaction Steps

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)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07888364B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-1931022aed4445298f0b877497034088
Source note	uspto-grants-2011_02