Potassium Carbonate → HCID 24785053, compound

HRID 1013051Notes

Reaction equation

HRID 1013051 reaction equation
[CH2:1]([C:3]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[N:4]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CC(=O)CC.O>[CH2:1]([C:3]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:14][CH:15]=2)[N:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 58256804HCID 58256804, compound

Product 1

HCID 24785053HCID 24785053, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(3,5-diethylpyrazol-1-yl)phenol (50 mg, 0.23 mmol) in 2-butanone (2 mL) was added potassium carbonate (35 mg, 0.25 mmol) and 1-(3-chloropropyl)pyrrolidine (37 mg, 0.25 mmol). The vial was capped and the reaction was heated overnight at 80° C. After the reaction was diluted with water and extracted with methylene chloride, the organic layer was dried (MgSO4) and concentrated. The residue was purified by semi-prep LC-MS to give 7.0 mg of the desired product. LC-MS (C20H29N3O calculated 327) m/z 328 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.29 (d, J=9.0 Hz, 2H), 6.94 (d, J=8.7 Hz, 2H), 6.02 (s, 1H), 4.05 (t, J=6.3 Hz, 2H), 2.73-2.54 (m, 10H), 2.06 (quint, J=6.3 Hz, 2H), 1.83 (s, 4H), 1.28 (t, J=7.5 Hz, 3H), 1.19 (t, J=7.5 Hz, 3H).

Workup

  1. customThe vial was capped
  2. extractionextracted with methylene chloride
  3. dry with materialthe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by semi-prep LC-MS

Sources & evidence

ORD record
ord-2aa411311ca14cb4a4cf43d09eb9a197
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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