Trifluoroacetic acid → HCID 59796800, compound

HRID 1524876Notes

Reaction equation

HRID 1524876 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[CH:12]=C(C#N)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[C:16]([OH:22])([C:18](F)(F)F)=[O:17].[H][H]>[Pt]=O>[NH2:8][C:7]1[C:6]2[CH2:9][CH2:10][CH:18]([C:16]([OH:22])=[O:17])[CH2:12][C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 87101212HCID 87101212, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59796800HCID 59796800, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Conditions

Temperature
60 °C

Procedure

The product from Example 147 Part D (1.0 g, 3.31 mmol) and platinum oxide (87 mg, 0.38 mmol) were added together with 21 mL of TFA. The reaction mixture was placed under a balloon of hydrogen gas and then warmed to 60° C. for 16 h. The mixture was cooled to RT and filtered through Celite to remove platinum oxide. The solvent was removed, and the residue was purified by reverse phase HPLC to give 0.21 g of the desired product as the TFA salt. LC/MS: 193.1, (M+H)+. 1HNMR (400 MHz, d4-MeOH) δ 2.00 (m, 1H), 2.28 (m, 1H), 2.57 (m, 2H) 2.85 (m, 1H), 3.02 (d, J=7.03 Hz, 2H), 6.75 (d, J=6.59 Hz, 1H), 7.61 (d, J=6.59 Hz, 1H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered through Celite
  3. customto remove platinum oxide
  4. customThe solvent was removed
  5. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-aaa0d9d50d3a4c7fa8966f586065a6d2
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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