Ethyl Acetate → HCID 131734598, compound

HRID 595862Notes

Reaction equation

HRID 595862 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:8][C:9]1[C:10]([NH2:29])=[N:11][CH:12]=[C:13]([C@@H:15]2[CH2:20][CH2:19][CH2:18][C@H:17]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:16]2)[N:14]=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:8][C:9]1[C:10]([NH:29][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[N:11][CH:12]=[C:13]([CH:15]2[CH2:20][CH2:19][CH2:18][CH:17]([O:21][Si:22]([C:25]([CH3:27])([CH3:26])[CH3:28])([CH3:23])[CH3:24])[CH2:16]2)[N:14]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 131734599HCID 131734599, compound

Product 1

HCID 131734598HCID 131734598, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Pivaloyl chloride (71.5 μL, 0.569 mmol) was added dropwise to a stirred, cooled (0° C.) mixture of (+/−)-3-bromo-5-((1R,3S)-3-((tert-butyldimethylsilyl)oxy)cyclohexyl)pyrazin-2-amine (110 mg, 0.285 mmol) and TEA (159 μL, 1.139 mmol) in CH2Cl2 (949 μL). The red mixture was stirred at 0° C. for 1 h, then at room temperature for 2 h. EtOAc and Sat NaHCO3 was added and stirred well. Organic layer was separated and the aqueous layer was extracted well with EtOAc. Combined EtOAc layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with EtOAc/heptane to give (+/−)-N-(3-bromo-5-(3-((tert-butyldimethylsilyl)oxy)cyclohexyl)pyrazin-2-yl)pivalamide 97 mg in 72.4% yield. LCMS (m/z): 472.3 (MH+), 1.19 min.

Workup

  1. temperaturecooled
  2. waitat room temperature for 2 h
  3. stirringstirred well
  4. customOrganic layer was separated
  5. extractionthe aqueous layer was extracted well with EtOAc
  6. washCombined EtOAc layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc/heptane

Sources & evidence

ORD record
ord-ced8e06d7a674890b51466410cb137b4
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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