Hydrochloric Acid → HCID 86670658, compound

HRID 1625049Notes

Reaction equation

HRID 1625049 reaction equation
Cl.[F:2][C:3]1[C:4]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:38]=[CH:37][O:36][N:35]=3)=[CH:30][CH:29]=2)=[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>O1CCOCC1>[F:2][C:3]1[C:4]([C:28]2[CH:29]=[CH:30][C:31]([C:34]3[CH:38]=[CH:37][O:36][N:35]=3)=[CH:32][CH:33]=2)=[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86670659HCID 86670659, compound

Product 1

HCID 86670658HCID 86670658, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.0 M aq HCl (15 mL) was added slowly to a solution of (2R)-4-[5-fluoro-4-(4-isoxazol-3-ylphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (655 mg, 1.23 mmol) in 1,4-dioxane (30 mL) at rt. The reaction was allowed to stir at rt overnight. The reaction was concentrated to a crude material. Water (30 mL) was added to the crude material and the mixture was boiled for 5 minutes. The mixture was allowed to cool to rt and the solid that formed was collected via filtration and dried under high vacuum to afford the title compound as a light yellow solid (314 mg, 56.9%). MS (APCI) m/z 450.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (s, 3 H) 2.10-2.21 (m, 1 H) 2.42-2.49 (m, 1 H) 3.09 (s, 3 H) 3.66-3.85 (m, 1 H) 3.96-4.09 (m, 1 H) 6.59 (d, J=7.61 Hz, 1 H) 7.21 (d, J=1.56 Hz, 1 H) 7.71 (dd, J=8.39, 1.76 Hz, 2 H) 8.00 (d, J=8.39 Hz, 2 H) 8.04 (d, J=6.44 Hz, 1 H) 9.03 (d, J=1.56 Hz, 1 H) 9.16-9.28 (m, 1 H) 11.06 (s, 1 H).

Workup

  1. concentrationThe reaction was concentrated to a crude material
  2. additionWater (30 mL) was added to the crude material
  3. waitthe mixture was boiled for 5 minutes
  4. temperatureto cool to rt
  5. customthe solid that formed
  6. filtrationwas collected via filtration
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-fc05ab05c42440678a3729e15d5e6685
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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