p-Toluenesulfonic acid → HCID 82415458, compound

HRID 1615248Notes

Reaction equation

HRID 1615248 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1COCC1.O>[NH2:15][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([CH:2]=[O:1])[CH:7]=2)[NH:11][N:10]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 68756246HCID 68756246, compound

Product 1

HCID 82415458HCID 82415458, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(1,3-dioxolan-2-yl)-1H-indazol-3-amine (75 mg, 0.36 mmol) in THF (5 mL) and H2O (0.5 mL) was added p-toluene sulfonic acid (25 mg) and the reaction was stirred overnight at room temperature. Ethyl acetate (75 mL) was added and the solution was washed with sat. sodium bicarbonate (5 mL), brine (2×5 mL), dried over MgSO4 and concentrated to give the title compound as an orange solid (52 mg, 89%). 1H NMR (400 MHz, CD3OD) δ 9.68 (s, 1H), 8.94 (s, 1H), 8.18 (d, 1H, J=7.6 Hz), 7.68 (d, 1H, J=8.4 Hz).

Workup

  1. washthe solution was washed with sat. sodium bicarbonate (5 mL), brine (2×5 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fe9e42457c164627a67e292cecb24d63
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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