Acetic Acid → HCID 57520574, compound

HRID 1528107Notes

Reaction equation

HRID 1528107 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH:23][C:24]3[C:33]4[C:28](=[C:29]([F:34])[CH:30]=[CH:31][CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[O:22])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>CN(C=O)C.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH:23][C:24]3[C:33]4[C:28](=[C:29]([F:34])[CH:30]=[CH:31][CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[O:22])[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 57520572HCID 57520572, compound

Product 1

HCID 57520574HCID 57520574, compoundYield 87.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

0.340 g of tert-butyl-6-[3-(8-fluoro-quinolin-4-yl)-ureido]-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylate (0.734 mmol) were dissolved in a mixture of 220 ml of DMF and 125 ml of methanol. After addition of 0.078 g of Pd/C (0.734 mmol) and 0.5 ml of acetic acid (8.73 mmol) hydrogenation was performed for 24 h 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. 300 mg of the desired product were obtained as a powder (yield: 88%).

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-98368fce124f46a7ae10aa66aed4ae45
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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