Cyclopropylamine → HCID 23090138, compound

HRID 1437303Notes

Reaction equation

HRID 1437303 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.[CH:28]1([NH2:31])[CH2:30][CH2:29]1>O1CCOCC1>[CH:28]1([NH:31][C:2]2[N:7]=[CH:6][C:5]([N:8]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:11][C:10]([C:19]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[O:20])=[N:9]3)=[CH:4][CH:3]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 23090270HCID 23090270, compound

Product 1

HCID 23090138HCID 23090138, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-[1-(6-chloro-3-pyridyl)-5-phenylpyrazole-3-carbonyl]-4-methylpiperazine (200 mg) obtained in Example 110 in dioxane (1.0 mL), cyclopropylamine (1.0 mL) was added. The mixture was stirred at 100° C. for 3 days in a sealed tube, and then cooled in air. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was sequentially washed with water and saturated aqueous sodium hydrogencarbonate, 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), to thereby give the title compound as an oily product (19.6 mg, 9%).

Workup

  1. temperaturecooled in air
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated aqueous sodium hydrogencarbonate
  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)

Sources & evidence

ORD record
ord-c999f7a0215242b38dfe7b3b71a51535
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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