Pyridine → HCID 11187117, compound

HRID 1766297Notes

Reaction equation

HRID 1766297 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([CH3:30])[CH:24]=[N:23]2.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([NH:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[C:25]([CH3:30])[CH:24]=[N:23]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 126667146-Quinoxalinamine,2-methyl-(9CI)

Product 1

HCID 11187117HCID 11187117, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (119 mg, 0.528 mmol) in dichloromethane (3 mL) was added pyridine (100 μL, 1.26 mmol) and the mixture was stirred under N2 for 5 min, after which time 6-amino-2-methylquinoxaline (80 mg, 0.50 mmol) was added. The resulting mixture was stirred for 5 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 a pale pink solid (161 mg, 92%), single spot at Rf 0.67 (ethyl acetate). mp 158.7-159.3° C., HPLC purity 99+% (tR 2.23 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 8.66 (1H, s), 8.02 (1H, d, J=7.7 Hz), 7.89 (1H, d, J=8.9 Hz), 7.61 (1H, d, J=2.5 Hz), 7.55 (1H, d, J=8.2 Hz), 7.46 (11H, dd, J=8.9, 2.5 Hz), 7.23 (1H, t, J=7.9 Hz), 7.08 (1H, s, N—H), 2.76 (3H, s), 2.71 (3H, s). LCMS: 346.11 (M−). FAB-MS (MH+, C16H14ClN3O2S): calcd 348.0573, found 348.0589.

Workup

  1. stirringThe resulting mixture was stirred for 5 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-d5f6920034024be3ac5c32dae89dcb40
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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