Acetic Acid → HCID 86625197, compound

HRID 419563Notes

Reaction equation

HRID 419563 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH3:2].[CH3:23][C:24]([OH:26])=[O:25]>[Pt]=O>[C:24]([OH:26])(=[O:25])[CH3:23].[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH:16][C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 59452604HCID 59452604, compound

Product 1

HCID 86625197HCID 86625197, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

N-[2-(Ethyloxy)-4-(4-pyridinyl)phenyl]-2,2,2-trifluoroacetamide (4.6 g, 14.82 mmol) was place in a 250 mL high pressure vessel and dissolved in 70 mL of HOAc. Platinum oxide (0.373 g, 1.48 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (60 psi). The solution stirred for 24 h. The vessel was evacuated and filled with N2 six times to remove any N H2. The solution was filtered through celite and evaporated to give the title compound of step E (4.8 g, 7.46 mmol, 98%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.27 (d, J=8.07 Hz, 1H), 6.94 (d, J=1.47 Hz, 1H), 6.81 (dd, J=8.07, 1.83 Hz, 1H), 4.05 (q, J=6.97 Hz, 2H), 3.20 (d, J=12.10 Hz, 2H), 2.79 (td, J=12.56, 2.38 Hz, 2H), 2.68-2.74 (m, 1H), 1.84 (s, 3H), 1.78-1.83 (m, 2H), 1.70 (td, J=12.56, 3.48 Hz, 2H), 1.28 (t, J=6.97 Hz, 3H).

Workup

  1. customThe flask was evacuated
  2. additionfilled with N2 six times
  3. customto remove any oxygen
  4. customThe vessel was evacuated
  5. additionfilled with N2 six times
  6. customto remove any N H2
  7. filtrationThe solution was filtered through celite
  8. customevaporated

Sources & evidence

ORD record
ord-f9a3f681738e43fc99e760ee06890790
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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