Potassium Phosphate, Tribasic → 5-(4-{2-[3-(5,6-Dihydro-7H-imidazo[2,1-c][1,2,4]triazol-7-yl)phenyl]ethyl}-1-piperazinyl)-2-methylquinoline

HRID 15902Notes

Reaction equation

HRID 15902 reaction equation
I[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][C:20]([CH3:26])=[N:21]4)[CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[NH:27]1[C:31]2=[N:32][CH2:33][CH2:34][N:30]2[CH:29]=[N:28]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:27]1[N:28]=[CH:29][N:30]2[CH2:34][CH2:33][N:32]([C:2]3[CH:3]=[C:4]([CH2:8][CH2:9][N:10]4[CH2:15][CH2:14][N:13]([C:16]5[CH:25]=[CH:24][CH:23]=[C:22]6[C:17]=5[CH:18]=[CH:19][C:20]([CH3:26])=[N:21]6)[CH2:12][CH2:11]4)[CH:5]=[CH:6][CH:7]=3)[C:31]=12

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 574443555-{4-[2-(3-Iodophenyl)ethyl]-1-piperazinyl)2-methylquinolineHCID 178420917HCID 178420917, compound

Product 1

HCID 574443775-(4-{2-[3-(5,6-Dihydro-7H-imidazo[2,1-c][1,2,4]triazol-7-yl)phenyl]ethyl}-1-piperazinyl)-2-methylquinolineYield 26%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-{4-[2-(3-Iodophenyl)ethyl]-1-piperazinyl}-2-methylquinoline (59 mg), 5,6-dihydro-1H-imidazo[2,1-c][1,2,4]triazole (50 mg, 3.5 equiv.), palladium(II) acetate (9 mg, 0.3 equiv.) 2-(dicyclohexylphosphino)-2′-methylbiphenyl (42 mg, 0.9 equiv.) and potassium phosphate (97 mg, 3.5 equiv.) were suspended in DME and stirred at 150 C under microwave irradiation for 2 h. The mixture was cooled to room temperature, diluted with methanol and loaded onto an ion-exchange cartridge (SCX-2), which was eluted with methanol followed by ammonia-methanol solution (1M). The combined basic fractions were concentrated under vacuum and purified using column chromatography [SiO2; DCM-MeOH (90:10)] to afford the title compound as colourless solid (13 mg, 26% yield).

Workup

  1. washwas eluted with methanol
  2. concentrationThe combined basic fractions were concentrated under vacuum
  3. custompurified

Sources & evidence

ORD record
ord-6471db98a5214e7cbe1a9be559977269
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Reaction notes

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