Potassium Carbonate → HCID 11325936, compound

HRID 2109934Notes

Reaction equation

HRID 2109934 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:17]1([C:22]2[CH:26]=[C:25]([NH2:27])[N:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[N:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:17]1([C:22]2[CH:26]=[C:25]([NH:27][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])[N:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[N:23]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acidHCID 58958606HCID 58958606, compound2×

Product 1

HCID 11325936HCID 11325936, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloronicotinic acid (113 mg, 0.72 mmol), potassium carbonate (199 mg, 1.44 mmol), 3-cyclopentyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (174 mg, 0.72 mmol) (Intermediate E), and copper (II) acetate (6.5 mg, 0.04 mmol) in DMF (3 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 59.7 mg (23%) of the desired product.

Workup

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

Sources & evidence

ORD record
ord-4e4ea3e3c81a410bb10461273e8cd313
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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