Cesium carbonate → 4-Methyl-3-[1-(2-oxo-1-pyrrolidinyl)-6-phthalazinyl]benzamide

HRID 2357668Notes

Reaction equation

HRID 2357668 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=3[CH3:21])[C:15]([NH2:17])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:38]1[CH2:42][CH2:41][CH2:40][C:39]1=[O:43]>CN(C=O)C.[Cu]I>[CH3:21][C:20]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][C:12]=1[C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([N:38]1[CH2:42][CH2:41][CH2:40][C:39]1=[O:43])=[N:3][N:4]=[CH:5]2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86607617HCID 86607617, compound

Product 1

HCID 684526484-Methyl-3-[1-(2-oxo-1-pyrrolidinyl)-6-phthalazinyl]benzamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

In a microwave tube was placed 3-(1-chlorophthalazin-6-yl)-4-methylbenzamide (0.150 g, 0.50 mmol), copper (I) iodide (0.0048 g, 0.025 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (0.014 g, 0.10 mmol), cesium carbonate (0.34 g, 1.1 mmol) and pyrrolidin-2-one (0.077 mL, 1.0 mmol) in 2 mL of DMF. The mixture was heated at 150°-200° C. for 20 minutes in the microwave. After cooling, the reaction was filtered through Celite®. Water was added to the filtrate and the mixture was extracted with dichloromethane (3×). The organic layer was concentrated and the crude material purified by HPLC to give 4-methyl-3-(1-(2-oxopyrrolidin-1-yl)phthalazin-6-yl)benzamide as white solid. Found MS (ES+)=347 (M+H+)

Workup

  1. customIn a microwave tube was placed
  2. temperatureThe mixture was heated at 150°-200° C. for 20 minutes in the microwave
  3. temperatureAfter cooling
  4. filtrationthe reaction was filtered through Celite®
  5. additionWater was added to the filtrate
  6. extractionthe mixture was extracted with dichloromethane (3×)
  7. concentrationThe organic layer was concentrated
  8. customthe crude material purified by HPLC

Sources & evidence

ORD record
ord-ab4943ea41a544eda4d34f4ae6b2b5f2
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

Loading…