Hydrochloric Acid → HCID 57635778, compound

HRID 2109938Notes

Reaction equation

HRID 2109938 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.Cl[C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C(OCC)(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:15]2[N:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])[N:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 708015-Amino-3-methyl-1-phenylpyrazoleHCID 762582-Chloronicotinic acid

Product 1

HCID 57635778HCID 57635778, compoundYield 18%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-methyl-1-phenyl-1H-pyrazol-5-amine (600 mg, 3.46 mmol) and 2-chloronicotinic acid (546 mg, 3.46 mmol) in DMF (6 mL), was added potassium carbonate (543 mg, 3.93 mmol) and copper (II) acetate (18 mg). The mixture was stirred at 150° C. for 18 h, and then cooled to rt, and diluted with ethyl acetate (2×) and water. The solution was adjusted to pH 2-3 using 1 N aqueous HCl. The mixture was extracted with EtOAc (3×5 mL), and then the combined organic extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by HPLC (20-90% acetonitrile in water) to afford the product (126 mg, 18%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.19 (s, 3H), 6.62 (s, 1H), 6.77 (m, 1H), 7.34 (m, 1H), 7.45 (m, 2H), 7.53 (m, 2H), 8.16 (d, 1H), 8.22 (d, 1H), 12.32 (s, 1H); ES-MS m/z 295.1 (MH+); HPLC RT (min) 2.17.

Workup

  1. temperaturecooled to rt
  2. extractionThe mixture was extracted with EtOAc (3×5 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by HPLC (20-90% acetonitrile in water)

Sources & evidence

ORD record
ord-03be33e3615d4406a08bc6865951ec54
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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