Water → PF-5081090

HRID 84246Notes

Reaction equation

HRID 84246 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C@@:18]([CH3:33])([S:29]([CH3:32])(=[O:31])=[O:30])[C:19]([NH:21][O:22]C2CCCCO2)=[O:20])[C:12](=[O:34])[CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C@@:18]([CH3:33])([S:29]([CH3:32])(=[O:30])=[O:31])[C:19]([NH:21][OH:22])=[O:20])[C:12](=[O:34])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22033616Pyridinium.p-toluenesulfonateHCID 86671932(2R)-4-[4-(2-Fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 56964907PF-5081090Yield 76.33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2R)-4-[4-(2-Fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (34.7 mg, 69.9 mmol) and pyridinium p-toluenesulfonic acid (8.8 mg, 34.9 mmol) were dissolved in ethanol (277.6 uL) and immersed in a 75° C. oil bath. The reaction was stirred at this temperature for 1 hour and allowed to cool. Water (600 uL) was added to the solution and the reaction was stirred overnight. A solid was collected via filtration and dried under vacuum to afford the title compound as an off-white powder (22 mg, 76.33%). LCMS m/z 413.5 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3 H) 2.11-2.22 (m, 1 H) 2.37-2.47 (m, 1 H) 3.10 (s, 3 H) 3.68-3.79 (m, 1 H) 3.82 (s, 3 H) 4.05-4.16 (m, 1 H) 6.44-6.50 (m, 1 H) 6.54 (s, 1 H) 6.89 (dd, J=8.68, 2.44 Hz, 1 H) 6.97 (dd, J=13.37, 2.44 Hz, 1 H) 7.54 (dd, J=8.98, 8.98 Hz, 1 H) 7.71 (d, J=7.02 Hz, 1 H) 11.14 (br. s., 1 H).

Workup

  1. customimmersed in a 75° C.
  2. temperatureto cool
  3. stirringthe reaction was stirred overnight
  4. filtrationA solid was collected via filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ad7b36c046ae45d8b3dd33513cf0326e
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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