Pyridine → HCID 11462138, compound

HRID 1766290Notes

Reaction equation

HRID 1766290 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]=[CH: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]=[CH:23]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1031482-Methylquinolin-6-amineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chloride

Product 1

HCID 11462138HCID 11462138, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (149 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 90 min 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 (148 mg, 68%), single spot at Rf 0.64 (ethyl acetate). mp 178.1-178.4° C., HPLC purity 99+% (tR 2.27 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.93-7.89 (3H, m), 7.53 (1H, d, J=8.2 Hz), 7.44 (1H, d, J=2.5 Hz), 7.31-7.24 (2H, m), 7.18 (1H, t, J=8.1 Hz), 2.73 (3H, s), 2.69 (3H, s). LCMS: 345.17 (M−). FAB-MS (MH+, C17H15CIN2O2S): calcd 347.0621, found 347.0622.

Workup

  1. stirringThe resulting mixture was stirred for 90 min at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (20 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-03f2a811b6c04fa1b1d8998fca62e668
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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