Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86670645, compound

HRID 1625031Notes

Reaction equation

HRID 1625031 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[F:18][C:19]1[C:20]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([O:50][CH3:51])[C:45]=2[F:52])=[CH:21][C:22](=[O:43])[N:23]([CH2:25][CH2:26][C@@:27]([CH3:42])([S:38]([CH3:41])(=[O:40])=[O:39])[C:28]([NH:30][O:31]C2CCCCO2)=[O:29])[CH:24]=1>C(O)C>[F:18][C:19]1[C:20]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([O:50][CH3:51])[C:45]=2[F:52])=[CH:21][C:22](=[O:43])[N:23]([CH2:25][CH2:26][C@@:27]([CH3:42])([S:38]([CH3:41])(=[O:40])=[O:39])[C:28]([NH:30][OH:31])=[O:29])[CH:24]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 86670646HCID 86670646, compound

Product 1

HCID 86670645HCID 86670645, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Pyridinium p-toluenesulfonate (190 mg, 0.76 mmol) was added to a solution of (2R)-4-[5-fluoro-4-(2-fluoro-3-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (777 mg, 1.51 mmol) in ethanol (15 mL). The reaction was heated to 50° C. and stirred at this temperature overnight. Additional pyridinium p-toluenesulfonate (118 mg, 0.47 mmol) was added to the solution and the reaction was heated at 60° C. for 3 h. The reaction was allowed to cool to rt and the precipitate was collected via filtration. The solid was washed with ethanol (15 mL) and hexanes (15 mL) and dried in vacuo to afford the title compound as a white solid (413 mg, 63.5%). MS (LCMS) m/z 431.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 1 H) 2.08-2.25 (m, 0 H) 2.41-2.56 (m, 1 H) 3.02-3.19 (m, 3 H) 3.71-3.85 (m, 1 H) 3.88 (s, 3 H) 3.98-4.13 (m, 1 H) 6.47 (d, J=7.02 Hz, 1 H) 6.93-7.08 (m, 1 H) 7.19-7.36 (m, 2 H) 8.04 (d, J=5.66 Hz, 1 H) 9.24 (d, J=1.56 Hz, 1 H) 11.07 (d, J=1.56 Hz, 1 H).

Workup

  1. temperaturethe reaction was heated at 60° C. for 3 h
  2. temperatureto cool to rt
  3. filtrationthe precipitate was collected via filtration
  4. washThe solid was washed with ethanol (15 mL) and hexanes (15 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ec7064408be946e6a3282e204da20ffd
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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