Hydrazine → HCID 178420748, compound

HRID 930555Notes

Reaction equation

HRID 930555 reaction equation
Cl[C:2]1[C:7]([C:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:15][NH2:16]>O1CCOCC1.ClCCl>[S:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[NH:16][N:15]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 23284507(2-Chloropyridin-3-yl)(1,3-thiazol-2-yl)methanone

Product 1

HCID 178420748HCID 178420748, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 2-chloro-3-[(2-thiazolyl)carbonyl]pyridine (257.5 mg, 1.2 mmol, 1 equiv) in dioxane (3 mL) in a sealed tube was added hydrazine (2 mL). The mixture was heated at 150° C. overnight, cooled to room temperature and concentrated in vacuo to provide a crude residue. The resultant residue was diluted with dichloromethane (300 mL), washed with water (50 mL) and brine (50 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide 3-thiazol-2-yl-1H-pyrazolo[3,4-b]pyridine (212.3 mg) as a yellow powder which used without further purification: LCMS (ES) M+H 203.5, Rf 2.68 min (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C., 1 ml/min flow rate, a 2.5 min gradient of 20% to 100% B with a 1.1 min wash at 100% B; A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto provide a crude residue
  4. washwashed with water (50 mL) and brine (50 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ec5caf12beb49f9b07dd4f4b5934279
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

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