Hydrochloric Acid → HCID 60172487, compound

HRID 1625044Notes

Reaction equation

HRID 1625044 reaction equation
Cl.[F:2][C:3]1[C:4]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[F:36])=[CH:5][C:6](=[O:27])[N:7]([CH2:9][CH2:10][C@@:11]([CH3:26])([S:22]([CH3:25])(=[O:24])=[O:23])[C:12]([NH:14][O:15]C2CCCCO2)=[O:13])[CH:8]=1.O>O1CCOCC1.C(Cl)Cl>[F:2][C:3]1[C:4]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[F:36])=[CH:5][C:6](=[O:27])[N:7]([CH2:9][CH2:10][C@@:11]([CH3:26])([S:22]([CH3:25])(=[O:24])=[O:23])[C:12]([NH:14][OH:15])=[O:13])[CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86670653HCID 86670653, compound

Product 1

HCID 60172487HCID 60172487, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl (4 M in 1,4-dioxane, 4.4 mL, 17.5 mmol) was added to a solution of (2R)-4-[5-fluoro-4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1.5 g, 2.9 mmol) in 1,4-dioxane (20 mL), DCM (20 mL), and water (5 mL) and the reaction was stirred for 20 min at rt. The reaction was concentrated under reduced pressure, isopropyl alcohol (10 mL) was added to the residue and the mixture was concentrated. Isopropyl alcohol (30 mL) was added to the residue and the solution was stirred overnight at rt to afford a precipitate. The precipitate was collected via filtration, washed with isopropyl alcohol, and dried under vacuum to afford the title compound as a light brown solid (725 mg, 58%) MS (LCMS) m/z 431.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3 H) 2.07-2.25 (m, 1 H) 2.42-2.48 (m, 1 H) 3.11 (s, 3 H) 3.71-3.81 (m, 1 H) 3.83 (s, 3 H) 4.00-4.11 (m, 1 H) 6.44 (d, J=7.02 Hz, 1 H) 6.92 (dd, J=8.59, 2.54 Hz, 1 H) 7.00 (dd, J=12.39, 2.44 Hz, 1 H) 7.42 (t, J=8.49 Hz, 1 H) 8.03 (d, J=5.85 Hz, 1 H) 9.25 (br. s., 1 H) 11.10 (s, 1 H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure, isopropyl alcohol (10 mL)
  2. additionwas added to the residue
  3. concentrationthe mixture was concentrated
  4. additionIsopropyl alcohol (30 mL) was added to the residue
  5. stirringthe solution was stirred overnight at rt
  6. customto afford a precipitate
  7. filtrationThe precipitate was collected via filtration
  8. washwashed with isopropyl alcohol
  9. customdried under vacuum

Sources & evidence

ORD record
ord-ccd1861e8f2f49f2b7a6f6f87601e676
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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