Acetic Acid → HCID 57520095, compound

HRID 1528100Notes

Reaction equation

HRID 1528100 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=2)=[O:19])[CH2:3][CH2:2]1.C(O)(=O)C>O1CCOCC1.C(O)C.[Pd]>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[N:22]=2)=[O:19])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 57520094HCID 57520094, compound

Product 1

HCID 57520095HCID 57520095, compoundYield 334.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

0.59 g of 1-(6-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl)-3-(6-(trifluoromethyl)pyridin-2-yl)urea (0.427 mmol) were dissolved in a mixture of 143 ml of dioxane and 10 ml of ethanol. After addition of 0.152 g of Pd/C (1.427 mmol) and 0.082 ml of acetic acid (1.427 mmol), hydrogenation was performed for 7 h at 60° C. and over night at room temperature, which led to complete double bond hydrogenation according to HPLC/MSD analysis. The catalyst was filtered off, the solvent removed under reduced pressure and the residue extracted three times with ethyl acetate after adding water and a small amount of NaOH (pH 9). The combined organic phases were washed with a small amount of brine, dried over sodium sulfate and the solvent was removed under reduced pressure. 593 mg of the desired product were obtained as light yellow powder (yield: 64%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. extractionthe residue extracted three times with ethyl acetate
  4. additionafter adding water
  5. washThe combined organic phases were washed with a small amount of brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9adc212ef427406b9357f07dd15f1dfe
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

Loading…