p-Toluenesulfonic acid monohydrate → HCID 25060876, compound

HRID 2380842Notes

Reaction equation

HRID 2380842 reaction equation
[CH:1]1([NH:4][C:5](=[O:33])[C:6]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]4[C:18]([C:21]([CH3:30])([O:23]C5CCCCO5)[CH3:22])=[N:19][N:20]=[C:14]4[CH:13]=3)[C:9]([CH3:31])=[C:8]([F:32])[CH:7]=2)[CH2:3][CH2:2]1.O.CC1C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:33])[C:6]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][N:15]4[C:18]([C:21]([OH:23])([CH3:30])[CH3:22])=[N:19][N:20]=[C:14]4[CH:13]=3)[C:9]([CH3:31])=[C:8]([F:32])[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 68712798HCID 68712798, compound

Product 1

HCID 25060876HCID 25060876, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-cyclopropyl-3-fluoro-4-methyl-5-{3-[1-methyl-1-(tetrahydro-2H-pyran-2-yloxy)ethyl][1,2,4]triazolo[4,3-a]pyridin-7-yl}benzamide (0.065 g, 0.14 mmol) in methanol (1 mL) was added 4-methylbenzenesulfonic acid hydrate (0.010 mg, 0.06 mmol). The reaction mixture was stirred at room temperature for 5 hours, the solvent was concentrated under reduced pressure and the oil obtained was dissolved in ethyl acetate. The organic layer was washed with an aqueous solution of sodium bicarbonate and brine, dried over anhydrous sodium sulphate and concentrated. The crude was treated with diethyl ether to obtain the title compound (78%) as a solid.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. customthe oil obtained
  3. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. additionThe crude was treated with diethyl ether

Sources & evidence

ORD record
ord-4684e02351334625adfd5ec41df5c953
Source dataset
uspto-grants-2012_09
Patent number
US08258122B2

Reaction notes

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