Water → 5-Chloro-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide

HRID 629892Notes

Reaction equation

HRID 629892 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.[S:11](N)(N)(=[O:13])=[O:12].N1C=CC=CC=1.O>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:9])[S:11](=[O:13])(=[O:12])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 82267SulfamideHCID 249039426-Chloro-N2-methylpyridine-2,3-diamine

Product 1

HCID 889057545-Chloro-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 6-chloro-N2-methylpyridine-2,3-diamine (1-2) (2.043 g, 12.96 mmol), sulfamide (2.69 g, 28.0 mmol), and anhydrous pyridine (20 ml). The reaction mixture was refluxed at 125 C in a hot oil bath with stirring under an atmosphere of nitrogen with a water cooled reflux condenser attached overnight (16 hours). The reaction mixture was then cooled to room temperature and suspended in EtOAc (250 mL) & 6N HCl in water (250 mL) and filtered. Filtrate was then separated, organics dried over sodium sulfate, filtered & concentrated. The resulting residue was then purified with silica gel chromatography (0-20% Isopropanol/DCM) & concentrated to yield 5-chloro-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (23-1). HRMS (M+H)+: observed=219.9946, calculated=219.9942.

Workup

  1. temperatureThe reaction mixture was refluxed at 125 C in a hot oil bath
  2. temperaturecooled
  3. temperaturereflux condenser
  4. custom(16 hours)
  5. filtration6N HCl in water (250 mL) and filtered
  6. customFiltrate was then separated
  7. dry with materialorganics dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was then purified with silica gel chromatography (0-20% Isopropanol/DCM)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0375304d841348ebb9a61d620c0108b8
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

Loading…