Dimethylformamide → HCID 23090411, compound

HRID 1437302Notes

Reaction equation

HRID 1437302 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][C:10]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[O:20])=[N:9]2)=[CH:4][CH:3]=1.[CH3:28][N:29](C)C=O>CN.CO>[CH3:28][NH:29][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][C:10]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[O:20])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 23090270HCID 23090270, compound

Product 1

HCID 23090411HCID 23090411, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 57454252Monomethylamine methanolSolvent

Procedure

To a solution of 1-[1-(6-chloro-3-pyridyl)-5-phenylpyrazole-3-carbonyl]-4-methylpiperazine (300 mg) obtained in Example 110 in N,N-dimethylformamide (1.5 mL), 40% methylamine-methanol solution (0.6 mL) was added. The mixture was stirred at 85>C for 3 days in a sealed tube, and then cooled in air. The reaction mixture was partitioned between 1N aqueous sodium hydroxide (30 mL) and ethyl acetate. The organic layer was sequentially washed with water, saturated aqueous sodium hydrogencarbonate, and water, and then dried over magnesium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure, and the residue was dissolved in dimethyl sulfoxide (1 mL). The solution was purified through preparative high-performance liquid chromatography (eluent: water acetonitrile), followed by recrystallization from ether-hexane, to thereby give the title compound (11.7 mg, 4%).

Workup

  1. temperaturecooled in air
  2. customThe reaction mixture was partitioned between 1N aqueous sodium hydroxide (30 mL) and ethyl acetate
  3. washThe organic layer was sequentially washed with water, saturated aqueous sodium hydrogencarbonate, and water
  4. dry with materialdried over magnesium sulfate anhydrate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in dimethyl sulfoxide (1 mL)
  8. customThe solution was purified through preparative high-performance liquid chromatography (eluent: water acetonitrile)
  9. customfollowed by recrystallization from ether-hexane

Sources & evidence

ORD record
ord-5f5657a32e02475fa3e98a6410f8a8a6
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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