Imidazole → HCID 131734596, compound

HRID 595855Notes

Reaction equation

HRID 595855 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH:9]=2)=[N:6][CH:7]=1.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].N1C=CN=C1>CN(C=O)C>[Si:19]([O:14][CH:10]1[CH2:11][CH2:12][CH2:13][C:8]([C:5]2[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)=[CH:9]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 118045610HCID 118045610, compound

Product 1

HCID 131734596HCID 131734596, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-aminopyrazin-2-yl)cyclohex-2-enol (149 mg, 0.779 mmol) in DMF (5.5 mL) at 0° C. were added tert-butylchlorodimethylsilane (294 mg, 1.95 mmol)) and 1H-imidazole (212 mg, 3.12 mmol). The reaction mixture was stirred at room temperature overnight. After quenched with sat NaHCO3, the reaction mixture was extracted with EtOAc 3 times. The combined organic layers were dried over anhydrous sodium sulfate. Filtered and concentrated in vacuo. The crude product was purified with flash chromatography eluting with 0-100% of EtOAc/heptane to provide 238 mg of crude product which was used as it was. LCMS (m/z): 306.9 (MH+), 1.04 min.

Workup

  1. customAfter quenched with sat NaHCO3
  2. extractionthe reaction mixture was extracted with EtOAc 3 times
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationFiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified with flash chromatography
  7. washeluting with 0-100% of EtOAc/heptane

Sources & evidence

ORD record
ord-83cf9afe2d0644599154ee857a649a84
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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