Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 49848306, compound

HRID 389868Notes

Reaction equation

HRID 389868 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:18][C:19]([C:29]1[CH:33]=[C:32]([NH:34][C:35]([C@@H:37]2[CH2:40][CH2:39][N:38]2[C:41]2[C:46]([Cl:47])=[CH:45][C:44]([C:48]([F:51])([F:50])[F:49])=[CH:43][N:42]=2)=[O:36])[O:31][N:30]=1)([CH3:28])[CH2:20][O:21]C1CCCCO1>C(O)C>[OH:21][CH2:20][C:19]([C:29]1[CH:33]=[C:32]([NH:34][C:35]([C@@H:37]2[CH2:40][CH2:39][N:38]2[C:41]2[C:46]([Cl:47])=[CH:45][C:44]([C:48]([F:51])([F:50])[F:49])=[CH:43][N:42]=2)=[O:36])[O:31][N:30]=1)([CH3:28])[CH3:18]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 67953732HCID 67953732, compound

Product 1

HCID 49848306HCID 49848306, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Pyridinium p-toluenesulfonate (13.3 mg; 0.053 mmol) is added to a solution of (S)-1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-azetidine-2-carboxylic acid {3-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-amide (204 mg; 0.406 mmol) in ethanol (2 mL). The reaction mixture is stirred at 55° C. for 5 hours and more pyridinium p-toluenesulfonate (15 mg; 0.060 mmol) is added and the reaction mixture is stirred at 55° C. for 18 hours. After this time, the reaction mixture is concentrated and then diluted with ethyl acetate. It is washed with saturated NaHCO3 aqueous solution. The layers are separated and the aqueous layer is extracted with ethyl acetate once. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/hexanes provides the title compound, m/z 419 [M+H+]

Workup

  1. stirringthe reaction mixture is stirred at 55° C. for 18 hours
  2. concentrationAfter this time, the reaction mixture is concentrated
  3. additiondiluted with ethyl acetate
  4. washIt is washed with saturated NaHCO3 aqueous solution
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with ethyl acetate once
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b1c4a9c946484aa1bb93ed0023af3c27
Source dataset
uspto-grants-2013_02
Patent number
US08383615B2

Reaction notes

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