Acetonitrile → HCID 68454221, compound

HRID 2357626Notes

Reaction equation

HRID 2357626 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>C(OCC)(=O)C>[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

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 placed in the microwave for 80 min at 200° C. before being diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give the crude product. After purification by chromatography, the title compound was obtained. MS (ES+): 377 (M+H)+.

Workup

  1. additionadded to a separation funnel
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. washwashed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customAfter purification by chromatography

Sources & evidence

ORD record
ord-b1a3f32570594734a6d60a36a44877d2
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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