HCID 59553907, compound → HCID 59553890, compound

HRID 1170913Notes

Reaction equation

HRID 1170913 reaction equation
C([O:8][C:9]1[C:10]([CH:15]2[NH:20][C:19]3[CH:21]=[CH:22][N:23]=[C:24]([C:25]([F:28])([F:27])[F:26])[C:18]=3[C:17](=[O:29])[N:16]2[CH:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)C.[Pd]>[F:39][C:34]1[CH:33]=[C:32]([CH2:31][CH:30]([N:16]2[C:17](=[O:29])[C:18]3[C:24]([C:25]([F:26])([F:27])[F:28])=[N:23][CH:22]=[CH:21][C:19]=3[NH:20][CH:15]2[C:10]2[C:9]([OH:8])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH3:40])[CH:37]=[CH:36][C:35]=1[F:38]

Participants

4

Reactant 1

HCID 59553907HCID 59553907, compound

Product 1

HCID 59553890HCID 59553890, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(3-(benzyloxy)pyridin-2-yl)-3-(1-(3,4-difluorophenyl)propan-2-yl)-5-(trifluoromethyl)-2,3-dihydropyrido[4,3-d]pyrimidin-4(1H)-one (4.61 g, 8.31 mmol) was dissolved in absolute ethanol (150 mL). To this was added 10% palladium on carbon (0.50 g) and the mixture was hydrogenated on a Parr shaker at 45 PSI for 2.5 hours. The reaction was filtered through celite, and the filter cake washed with ethanol. The combined filtrates were concentrated in vacuo to an oil. This oil was purified by silica gel column chromatography using 20%-40% acetone/hexanes as eluant to yield the product diastereomers as a pale yellow foam (3.86 g, 77% yield).

Workup

  1. filtrationThe reaction was filtered through celite
  2. washthe filter cake washed with ethanol
  3. concentrationThe combined filtrates were concentrated in vacuo to an oil
  4. customThis oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bab451c3ccfe46d2b6608e6abb05251d
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

Loading…