Imidazole → HCID 10265302, compound

HRID 1063103Notes

Reaction equation

HRID 1063103 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([N:12]([CH3:14])[CH3:13])=[CH:8][C:9]=2[CH3:11])[S:4][C:3]=1[C:15]([NH2:17])=[O:16].[NH:18]1C=CN=[CH:19]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.CCOC(C)=O>[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([N:12]3[CH:13]=[CH:19][N:18]=[CH:14]3)=[CH:8][C:9]=2[CH3:11])[S:4][C:3]=1[C:15]([NH2:17])=[O:16]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 10340Sodium CarbonateHCID 10060670HCID 10060670, compound

Product 1

HCID 10265302HCID 10265302, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 20 mg (0.067 mmol) of starting 4-methylpyridine triflate intermediate (see Example 2) in 1.2 mL of 1,4-dioxane was added 9.2 mg of imidazole. The resulting mixture was stirred for 2 h at 80° C. After that time 0.5 mL of 2M solution of sodium carbonate was added. The stirring was continued overnight at 100° C. The reaction mixture was then cooled to room temperature, diluted with EtOAc, dried with sodium sulfate and concentrated. The crude product was chromatographed (preparative TLC on silica gel eluting with 10% MeOH/methylene chloride, Rf=0.56) to afford 3.7 mg of product, which was further purified by HPLC (reverse phase—solvent system: isocratic 60% water/acetonitrile providing 2.7 mg (14.7%) of the title compound.

Workup

  1. waitThe stirring was continued overnight at 100° C
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was chromatographed (preparative TLC on silica gel eluting with 10% MeOH/methylene chloride, Rf=0.56)

Sources & evidence

ORD record
ord-8c986c049a2e44ab9771c0c58a28a418
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

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