Hydrazine → HCID 178420748, compound

HRID 390531Notes

Reaction equation

HRID 390531 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-eabb9e5813654b1686882b0455d8ea95
Source dataset
uspto-grants-2013_02
Patent number
US08383630B2

Reaction notes

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