Nitrogen → HCID 21110321, compound

HRID 1766296Notes

Reaction equation

HRID 1766296 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.N#N.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[C:28]([CH3:33])[C:27]([CH3:34])=[N:26]2.C([O-])(O)=O.[Na+]>ClCCl>[CH3:33][C:28]1[C:27]([CH3:34])=[N:26][C:25]2[C:30](=[CH:31][CH:32]=[C:23]([NH:22][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:24]=2)[N:29]=1

Participants

7

Reactant 5

HCID 947NitrogenHCID 1049PyridineHCID 1460536-Quinoxalinamine, 2,3-dimethyl-HCID 516892Sodium BicarbonateHCID 27372224-N-Propylbenzenesulphonyl chloride

Product 1

HCID 21110321HCID 21110321, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.4n-propylbenzenesulphonyl chloride (106 mg, 0.485 mmol) in dichloromethane (3 mL) was added pyridine (90 μL, 1.2 mmol) and the mixture was stirred under. N2 for 5 min, after which time 6-amino-2,3-dimethylquinoxaline (80 mg, 0.46 mmol) was added. The resulting mixture was stirred for 6 h at room temperature, then saturated NaHCO3 solution (8 mL) was added and the mixture was extracted into ethyl acetate (15 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 (147 mg, 90%), single spot at Rf 0.69 (ethyl acetate). mp 198.4-198.8° C., HPLC purity 99+% (tR 2.39 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.86 (1H, d, J=8.9 Hz), 7.72 (2H, d, Jz;8.4 Hz), 7.56 (1H, d, J=2.5 Hz), 7.48 (1H, dd, J9.2, 2.5 Hz), 7.20 (2H, d, J=7.9 Hz), 6.82 (1H, s, N—H, 2.67 (6H, s), 2.56 (2H, t, J=7.5 Hz), 1.57 (2H, sextet, J=7.4 Hz), 0.87 (3H, t, J=7.4 Hz). LCMS: 354.31 (M−). FAB-MS (MH+, C19H21N3O2S): calcd 356.1432, found 356.1433.

Workup

  1. stirringThe resulting mixture was stirred for 6 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (15 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Sources & evidence

ORD record
ord-58e618341a164541994e989bcfe656a7
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

Loading…