Methanol → HCID 57467467, compound

HRID 1890794Notes

Reaction equation

HRID 1890794 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]([NH2:8])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CO>C(Cl)Cl>[F:1][C:2]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]#[N:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 57467466HCID 57467466, compound

Product 1

HCID 57467467HCID 57467467, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 51A (0.9 g, 4.0 mmol) in methylene chloride (10 mL) and triethylamine (2.2 mL, 15.8 mmol) was added 2,2,2-trifluoroacetic anhydride (1.6 mL, 11.9 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for three hours before methanol was added to quench the reaction. The reaction mixture was washed with saturated aqueous NaHCO3 solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% methanol/ethyl acetate(1/10) in hexanes) to obtain the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.71 (s, 6H), 7.08-7.18 (m, 1H), 7.36-7.49 (m, 2H).

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. washThe reaction mixture was washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-44c437e655ad4dc0b5c70ea3c452657a
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

Loading…