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 468647Notes

Reaction equation

HRID 468647 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, 3H) 2.08-2.27 (m, 0H) 2.38-2.59 (m, 1H) 3.12 (s, 3H) 3.72-3.90 (m, 1H) 4.00-4.17 (m, 1H) 6.62 (d, J=7.61 Hz, 1H) 7.70-7.88 (m, 2H) 8.08 (d, J=6.63 Hz, 1H) 8.12-8.18 (m, 2H) 8.19 (s, 2H) 9.25 (d, J=1.95 Hz, 1H) 11.09 (d, J=1.76 Hz, 1H).

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-671c099019fa41ddb3b4a842ca5d5f1c
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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