p-Toluenesulfonic acid → HCID 59018176, compound

HRID 1455278Notes

Reaction equation

HRID 1455278 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]1([C:15]2[C:19]([O:20][C:21]3[CH:28]=[C:27]([CH3:29])[C:24]([C:25]#[N:26])=[C:23]([CH3:30])[CH:22]=3)=[CH:18][NH:17][N:16]=2)[CH2:14][CH2:13]1.[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1>O1CCCC1>[CH:12]1([C:15]2[C:19]([O:20][C:21]3[CH:28]=[C:27]([CH3:29])[C:24]([C:25]#[N:26])=[C:23]([CH3:30])[CH:22]=3)=[CH:18][N:17]([CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][O:31]3)[N:16]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 178428865HCID 178428865, compound

Product 1

HCID 59018176HCID 59018176, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Toluenesulphonic acid (20 mg, 0.12 mmol) was added to a solution of the benzonitrile of Example 16 (1 g, 3.94 mmol) in tetrahydrofuran (30 ml). 3,4-Dihydro-2H-pyran (664 mg, 7.9 mmol) was then added dropwise at room temperature. The reaction mixture was stirred at room temperature, under nitrogen, for 15 hours. It was then evaporated under reduced pressure and the residue was partitioned between ethyl acetate (100 ml) and aqueous sodium bicarbonate (50 ml). The organic layers were washed with brine (50 ml), dried over sodium sulphate, filtered and concentrated under reduced pressure to provide the title compound (1.93 mg, 100%).

Workup

  1. customIt was then evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (100 ml) and aqueous sodium bicarbonate (50 ml)
  3. washThe organic layers were washed with brine (50 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-558815634c604522b72a62f999399a5f
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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