Acetonitrile → HCID 68454221, compound

HRID 2357610Notes

Reaction equation

HRID 2357610 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[CH:13]([NH:16][C:17]([C@H:19]1[CH2:23][CH2:22][CH:21]([CH3:24])[NH:20]1)=[O:18])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:20]1[CH:21]([CH3:24])[CH2:22][CH2:23][C@@H:19]1[C:17]([NH:16][CH:13]([CH3:15])[CH3:14])=[O:18])=[N:7][N:6]=[CH:5]2

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 220304246-Bromo-1-chlorophthalazineHCID 68455343HCID 68455343, compound

Product 1

HCID 68454221HCID 68454221, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

6-Bromo-1-chlorophthalazine (215 mg, 881 μmol), (R)-N-isopropyl-5-methylpyrrolidine-2-carboxamide (150 mg, 881 μmol), and cesium carbonate (1435 mg, 4405 μmol) were added to acetonitrile (4.4 mL) and heated in the microwave oven for 80 min at 200° C. The reaction was diluted with 75 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 3× with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give crude. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 377(M+H)+.

Workup

  1. additionadded to an addition funnel
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. washThe organic layer was washed 3× with 50 mL of sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap
  7. customto give crude
  8. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-450ce89441b64eccba7c8502418fc516
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

Loading…