Potassium Carbonate → 2-{[3-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}nicotinamide

HRID 2109940Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:28]=[C:27]([NH2:29])[N:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])[N:25]=2)=[CH:20][CH:19]=1>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:28]=[C:27]([NH:29][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4]([NH2:6])=[O:5])[N:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])[N:25]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-chloronicotinamide (59 mg, 0.37 mmol), potassium carbonate (57 mg, 0.41 mmol), 3-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-amine (100 mg, 0.37 mmol) (Intermediate G), and copper (II) acetate (1.4 mg, 0.007 mmol) in DMF (1 mL) was heated (150° C.) in a sealed tube for 16 h. The mixture was cooled to rt, filtered through a silica gel plug using ethyl acetate as eluent, concentrated to dryness, and subjected to HPLC purification using a gradient elution from 30% to 90% acetonitrile in water to afford 20 mg (14%) of the desired product.

Workup

temperatureThe mixture was cooled to rt
filtrationfiltered through a silica gel plug
concentrationconcentrated to dryness
customsubjected to HPLC purification
washa gradient elution from 30% to 90% acetonitrile in water

Sources & evidence

ORD record: ord-475bb33dd2c644668cf1e08030286d55
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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