Hydrochloric Acid → HCID 86671925, compound

HRID 84242Notes

Reaction equation

HRID 84242 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][C@@:24]([CH3:39])([S:35]([CH3:38])(=[O:37])=[O:36])[C:25]([NH:27][O:28]C2CCCCO2)=[O:26])[C:18](=[O:40])[CH:17]=1.Cl.O>O1CCOCC1.CO>[F:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][C@@:24]([CH3:39])([S:35]([CH3:38])(=[O:36])=[O:37])[C:25]([NH:27][OH:28])=[O:26])[C:18](=[O:40])[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86671926(2R)-4-{4-[2-fluoro-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86671925HCID 86671925, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

(2R)-4-{4-[2-fluoro-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (335 mg, 0.58 mmol) was dissolved in 3 mL of dioxane. To this solution was added 1 mL of 4M HCl in dioxane 1 mL of water. The resulting solution was stirred at RT for 10 minutes. The material was diluted up with methanol and concentrated (3×). Dichloromethane was added and the mixture was stirred for 18 h. The solution retained color and a fine particulate was suspended. The mixture was filtered leaving 13.3 mg (6%) of white solid. LCMS m/z 413.6 (M+1) 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.71 (s, 3 H) 2.14 (d, J=1.56 Hz, 3 H) 2.33-2.46 (m, 1 H) 2.54-2.68 (m, 1 H) 3.10 (s, 3 H) 3.91-4.05 (m, 1 H) 4.24-4.40 (m, 1 H) 6.70 (d, J=8.59 Hz, 1 H) 6.75-6.86 (m, 2 H) 7.23 (t, J=8.68 Hz, 1 H) 7.75 (d, J=6.83 Hz, 1 H)

Workup

  1. concentrationconcentrated (3×)
  2. additionDichloromethane was added
  3. stirringthe mixture was stirred for 18 h
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-85dc97ad8b7540ac8d79f6feab6d52a6
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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