Methanol → HCID 67281584, compound

HRID 1187482Notes

Reaction equation

HRID 1187482 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:21])[CH:11]=[C:12]([CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][NH2:23].CO>ClCCl>[CH2:1]([O:8][C:9]1[C:10](=[O:21])[CH:11]=[C:12]([CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[N:23]([CH3:22])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 86623502HCID 86623502, compound

Product 1

HCID 67281584HCID 67281584, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In each of four parallel synthesis tubes equipped with a magnetic stir bar was placed 5-benzyloxy-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-pyran-4-one (0.90 g, 3.0 mmol), and a 2M methylamine solution in MeOH (5.5 mL, 11 mmol). The resulting solution was heated to reflux. The reaction was completed in 60 min. The solutions from the four reaction tubes were combined, and evaporated to dryness to give a semi solid mixture. The mixture was taken up in dichloromethane (15 mL) to give a thick solution. On standing, a solid product precipitated out to give the first crop of the title compound (2.90 g, 77% yield, HPLC Method 1 (Example 24); RT=13.0 min, HPLC purity (peak percent area): 99.5% at λ=280 nm). 1H NMR (DMSO-d6+D2O) δ ppm: 7.64 (s, 1H), 7.37 (m, 5H), 6.49 (s, 1H), 5.38 (q, J=6.5 Hz, 1H), 4.97 (s, 2H), 3.69 (s, 3H).

Workup

  1. customIn each of four parallel synthesis tubes
  2. customequipped with a magnetic stir bar
  3. temperatureThe resulting solution was heated to reflux
  4. customThe solutions from the four reaction tubes
  5. customevaporated to dryness
  6. customto give a semi solid mixture
  7. customto give a thick solution
  8. customa solid product precipitated out

Sources & evidence

ORD record
ord-3138d88e12b54f9d900ec9e413435132
Source dataset
uspto-grants-2014_03
Patent number
US08673943B2

Reaction notes

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