P-Toluenesulfonylhydrazide → HCID 178434588, compound

HRID 1170362Notes

Reaction equation

HRID 1170362 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[C:21](=O)[CH3:22])=[CH:15][CH:14]=1.C1(C)C=CC(S([NH:39][NH2:40])(=O)=O)=CC=1>C(O)(=O)C>[CH3:22][C:21]1[C:20]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[CH:14][CH:15]=2)[NH:40][N:39]=1

Participants

4

Reactant 2

HCID 15303P-Toluenesulfonylhydrazide2×HCID 685784954-(4-((Quinolin-2-yl)methoxy)phenyl)-3-(pyridin-4-yl)but-3-en-2-one

Product 1

HCID 178434588HCID 178434588, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(4-((quinolin-2-yl)methoxy)phenyl)-3-(pyridin-4-yl)but-3-en-2-one (1.00 g, 2.60 mmol) and p-toluensulfonylhydrazine (484 mg, 2.6 mmol) in acetic acid (14 mL) was heated at reflux for 10 h. Additional p-toluenesulfonylhydrazine (242 mg, 0.5 mmol) was added and the mixture heated at reflux 2 h. The mixture was concentrated, the residue dissolved in dichloromethane and the resulting solution washed with water (2×25 mL), dried and concentrated. The residue was chromatographed on silica eluted with 1%, 2%, and 3% methanol in dichloromethane containing 0.5% concentrated ammonium hydroxide giving a solid which was triturated with ether and dried. Yield 293 mg, 29%. 1H NMR (CDCl3, 400 mHz) δ 8.51 (m, 2H), 8.18 (d, 1H, J=8.7 Hz), 8.06 (d, 1H, J=7.9 Hz), 7.81 (d, 1H, J=8.3 Hz), 7.72 (m, 1H), 7.64 (d, 1H, J=8.3 Hz), 7.54 (m, 1H), 7.24 (m, 2H), 7.13 (m, 2H), 6.96 (m, 2H), 5.36 (s, 2H), 2.33 (s, 3H). HPLC-MS (system 1) 4.65 min, m/e 393 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 h
  3. temperaturethe mixture heated
  4. temperatureat reflux 2 h
  5. concentrationThe mixture was concentrated
  6. dissolutionthe residue dissolved in dichloromethane
  7. washthe resulting solution washed with water (2×25 mL)
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica
  11. washeluted with 1%, 2%, and 3% methanol in dichloromethane containing 0.5% concentrated ammonium hydroxide giving a solid which
  12. customwas triturated with ether
  13. customdried
  14. customHPLC-MS (system 1) 4.65 min, m/e 393 (MH+)

Sources & evidence

ORD record
ord-73394eca65524781a8ad065b5c8444da
Source dataset
uspto-grants-2010_11
Patent number
US07825254B2

Reaction notes

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