Potassium Carbonate → HCID 67243790, compound

HRID 2424416Notes

Reaction equation

HRID 2424416 reaction equation
Br[CH2:2][C:3]1[CH:7]=[CH:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:4]=1.[CH3:15][C@@H:16]1[CH2:21][NH:20][CH2:19][C@H:18]([CH3:22])[NH:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][C@H:16]1[NH:17][C@@H:18]([CH3:22])[CH2:19][N:20]([CH2:2][C:3]2[CH:7]=[CH:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:4]=2)[CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 23573257tert-Butyl 3-(bromomethyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 67243790HCID 67243790, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

D6 (1.67 g, 6.41 mmol), (2R,6S)-2,6-dimethylpiperazine (0.73 g, 6.41 mmol) and potassium carbonate (1.95 g, 14.1 mmol) in DMF (20 ml) were heated at 50° C. for 2 h. The mixture was concentrated and the residue partitioned between DCM and water (50 ml each). The aqueous layer was re-extracted with DCM (50 ml) and the combined organics washed with brine (100 ml), dried (Na2SO4) and concentrated to yield the title compound as an orange oil (1.88 g). δH (CDCl3) 1.25 (6H, d), 1.15 (1H, br s), 1.64-1.71 (11H, m), 2.77 (2H, m), 2.93 (2H, m), 3.59 (2H, s), 6.40 (1H, d), 8.00 (1H, d). MS (ES): MH+ 295

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between DCM and water (50 ml each)
  3. extractionThe aqueous layer was re-extracted with DCM (50 ml)
  4. washthe combined organics washed with brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-65d8ede4dfba452f906e3e4cc81351dd
Source dataset
uspto-grants-2011_06
Patent number
US07964602B2

Reaction notes

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