Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 1625043Notes

Reaction equation

HRID 1625043 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][C:47]([N:50]3[N:54]=[CH:53][CH:52]=[N:51]3)=[CH:46][CH:45]=2)=[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:45]=[CH:46][C:47]([N:50]3[N:54]=[CH:53][CH:52]=[N:51]3)=[CH:48][CH:49]=2)=[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)HCID 86670652(2R)-4-{5-fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 60199135(2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Pyridinium p-toluenesulfonate (360 mg, 0.50 mmol) was added to a solution of (2R)-4-{5-fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1.53 g, 2.87 mmol) in ethanol (60 mL). The solution was heated to 70° C. and was stirred at this temperature for 3 h. The reaction was allowed to cool and was stirred at rt for three days. The solid was collected via filtration, washed with ethanol (20 mL) and hexanes (20 mL). The solid was dried under vacuum to afford the title compound as a white solid (1.05 g, 81.5%). MS (LCMS) m/z 450.0 (M+1), 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3 H) 2.08-2.27 (m, 0 H) 2.38-2.59 (m, 1 H) 3.12 (s, 3 H) 3.72-3.90 (m, 1 H) 4.00-4.17 (m, 1 H) 6.62 (d, J=7.61 Hz, 1 H) 7.70-7.88 (m, 2 H) 8.08 (d, J=6.63 Hz, 1 H) 8.12-8.18 (m, 2 H) 8.19 (s, 2 H) 9.25 (d, J=1.95 Hz, 1 H) 11.09 (d, J=1.76 Hz, 1 H).

Workup

  1. temperatureto cool
  2. stirringwas stirred at rt for three days
  3. filtrationThe solid was collected via filtration
  4. washwashed with ethanol (20 mL) and hexanes (20 mL)
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-8433f2de090145889ecfe35911195433
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

Loading…