N,N'-Dimethylethylenediamine → HCID 25118690, compound

HRID 2400573Notes

Reaction equation

HRID 2400573 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)[N:14]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.C(OCC)(=O)C.O.O1CCOCC1>[CH3:18][C:16]1[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[N:14]=[C:13]([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:27]4[CH2:31][CH2:30][CH2:29][C:28]4=[O:32])=[CH:3][CH:4]=3)[N:12]=2)[CH:17]=1

Participants

9

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 25118340HCID 25118340, compound

Product 1

HCID 25118690HCID 25118690, compoundYield 40.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(4-iodophenyl)-5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazole (Example 13, 200 mg, 0.44 mmol), pyrrolidinone (67 μl, 0.88 mmol), potassium phosphate (186 mg, 0.88 mmol), copper(I) iodide (25 mg, 0.13 mmol), N,N′-dimethylethylenediamine (28 μl, 0.26 mmol) and 1,4-dioxane (4 ml) was stirred at 70° C. for 15 h. The reaction mixture was cooled and water (100 mL) and ethyl acetate (100 mL) was added. The layers were separated and the organic layer was washed with water and brine and then dried with magnesium sulfate. The solvent was evaporated and the residue was purified using preparative HPLC, to afford the title compound as a white solid (73 mg, 40%): 1H NMR (400 MHz, CDCl3) 8.21 (d, 2H), 7.79 (d, 2H), 7.13 (d, 2H), 7.08 (d, 2H), 6.79 (s, 1H), 5.41 (s, 2H), 3.93 (t, 2H), 2.65 (t, 2H), 2.33 (s, 3H), 2.26 (s, 3H), 2.20 (quint, 2H); ES-MS m/z 414 (MH)+, HPLC RT (Method E) 4.82 min.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe layers were separated
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified

Sources & evidence

ORD record
ord-e4e4c8f9c5b747a5a1e608aa331cc595
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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