Water → 6-{5-amino-6-[(1-methyl-1H-imidazol-5-yl)ethynyl]-3-phenyl-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone

HRID 915056Notes

Reaction equation

HRID 915056 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:10]=[C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[N:21]=2)=[N:13][C:14]=1Br.[C:32]([C:34]1[N:38]([CH3:39])[CH:37]=[N:36][CH:35]=1)#[CH:33].O>C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:8][C:9]1[N:10]=[C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[N:21]=2)=[N:13][C:14]=1[C:33]#[C:32][C:34]1[N:38]([CH3:39])[CH:37]=[N:36][CH:35]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 33331065-Ethynyl-1-methyl-1H-imidazoleHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 113044556-{5-amino-6-[(1-methyl-1H-imidazol-5-yl)ethynyl]-3-phenyl-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinoneYield 84.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In the presence of copper(I) iodide (3.7 mg) and dichlorobis(triphenylphosphine)palladium(II) (13.7 mg), triethylamine (0.0596 ml) was dropwise added to a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg) and 5-ethynyl-1-methyl-1H-imidazole (45.4 mg) in THF (1.5 ml) at 50° C. The mixture was refluxed for 2 hours. Water was added to the reaction mixture to give a solid. The solid was purified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (2:98 v/v) to give 6-{5-amino-6-[(1-methyl-1H-imidazol-5-yl)ethynyl]-3-phenyl-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone as a solid (135 mg).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customto give a solid
  3. customThe solid was purified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (2:98 v/v)

Sources & evidence

ORD record
ord-0270303b61b644139c9b2d837681ebec
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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