Methanol → HCID 57467473, compound

HRID 1890798Notes

Reaction equation

HRID 1890798 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([NH2:10])=O)=[C:4]([F:15])[CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CO>ClCCl>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]#[N:10])=[C:4]([F:15])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 57467472HCID 57467472, compound

Product 1

HCID 57467473HCID 57467473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 53C (8 g, 34.5 mmol) in dichloromethane (100 mL) and triethylamine (19.25 mL, 138 mmol) was added trifluoroacetic anhydride (slow addition, 14.63 mL, 104 mmol) at 0° C. After the addition, the solution was allowed to warm to room temperature and stirred for 2 hours before methanol (20 mL) was added to quench the reaction. The solution was washed with saturated NaHCO3 solution, dried (Na2SO4), and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-60% ethyl acetate in hexanes) to provide titled product. MS (DCI+) m/z 214 (M+H)+.

Workup

  1. additionAfter the addition
  2. additionwas added
  3. customto quench
  4. customthe reaction
  5. washThe solution was washed with saturated NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c6327ce61f9f429e84cc46a484d833a7
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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