Potassium Phosphate, Tribasic → HCID 71252555, compound

HRID 2412101Notes

Reaction equation

HRID 2412101 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:57][N:58]([CH3:67])[C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)=[O:60]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.COCCOC>[CH3:57][N:58]([CH3:67])[C:59]([N:61]1[CH2:62][CH2:63][N:64]([C:20]2[CH:21]=[CH:22][C:17]([C:15]([N:12]3[CH2:13][CH2:14][N:9]([C:3]4[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=4)[CH2:10][CH2:11]3)=[O:16])=[CH:18][CH:19]=2)[CH2:65][CH2:66]1)=[O:60]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 712909n,n-Dimethylpiperazine-1-carboxamideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 58484535[4-(3,5-Dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone

Product 1

HCID 71252555HCID 71252555, compoundYield 20.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl](4-iodophenyl)methanone (270 mg) described in Preparation Example 113, palladium acetate (8 mg), 2-(dicyclohexylphosphino)biphenyl (22 mg), tripotassium phosphate (190 mg) and piperazine-1-carboxylic acid dimethylamide (111 mg) was added 1,2-dimethoxyethane (5 mL), and the mixture was stirred with heating under reflux for 7 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by NH coated silica gel column chromatography (ethyl acetate:hexane) to give the title compound (58 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 7 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by NH coated silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-d95a029a48b14e6484523c25214ce8a2
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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