Pyridine → HCID 21110322, compound

HRID 1766291Notes

Reaction equation

HRID 1766291 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].N1C=CC=CC=1.[NH2:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[C:26]([CH3:31])[CH:25]=[CH:24]2.C([O-])(O)=O.[Na+]>ClCCl>[CH3:31][C:26]1[CH:25]=[CH:24][C:23]2[C:28](=[CH:29][CH:30]=[C:21]([NH:20][S:10]([C:7]3[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH:22]=2)[N:27]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1031482-Methylquinolin-6-amineHCID 516892Sodium BicarbonateHCID 27372224-N-Propylbenzenesulphonyl chloride

Product 1

HCID 21110322HCID 21110322, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution- of 0.4n-propylbenzenesulphonyl chloride (145 mg, 0.664 mmol) in dichloromethane (4 mL) was added pyridine (130 μL, 1.58 mmol) and the mixture was stirred- under N2 for 5 min, after which time 6-amino-2-methylquinoline (100 mg, 0.632 mmol) was added. The resulting mixture was stirred for 1 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford an off-white solid (186 mg, 86%), single spot at Rf 0.70 (ethyl acetate). mp 173.7-174.0° C., HPLC purity 99+% (tR 2.32 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.94 (1H, d, J=8.4 Hz), 7.89 (1H, d, J=9.2 Hz), 7.67 (2H, d, J=8.4 Hz), 7.54 (1H, d, J=2.5 Hz), 7.31 (1H, dd, J=8.9, 2.5 Hz), 7.25 (1H, d, J=8.4 Hz), 7.19 (2H, d, J=8.4 Hz), 7.07 (1H, s, N—H), 2.70 (3H, s), 2.56 (2H, t, J=7.5 Hz), 1.58 (2H, sextet, J=7.4 Hz), 0.87 (3H, t, J=7.4 Hz). LCMS: 339.24 (M−). FAB-MS (MH+, C19H20N2O2S): calcd 341.1323, found 341.1324.

Workup

  1. extractionthe mixture was extracted into ethyl acetate (20 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a residue that
  7. customwas purified

Sources & evidence

ORD record
ord-63635f7e684e45948428ff29ac641cae
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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