HCID 131730200, compound → HCID 59526378, compound

HRID 386018Notes

Reaction equation

HRID 386018 reaction equation
C[CH:2]([N:11](C([O-])=O)[C:12]([O:14][C:15](C)(C)C)=[O:13])[C:3]1[C:4]([CH3:10])=[N:5][C:6]([Cl:9])=[CH:7][CH:8]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:15][O:14][C:12](=[O:13])[NH:11][CH2:2][C:3]1[C:4]([CH3:10])=[N:5][C:6]([Cl:9])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 131730200HCID 131730200, compound

Product 1

HCID 59526378HCID 59526378, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl methyl[(6-chloro-2-methylpyridin-3-yl)methyl]imidodicarbonate (830 mg, 2.64 mmol) was taken up in a mixture of CH2Cl2 (8.0 ml) and TFA (2.0 ml) and stirred at room temperature for 1 h. The solution was concentrated, diluted with EtOAc, and washed with saturated NaHCO3. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (25-100% EtOAc/hexanes) afforded the title compound as a colorless solid.

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-704ae23b4de64dcdbd4ab0321016b1e9
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…