Hydrazine hydrate (1:1) → HCID 57973794, compound

HRID 1863936Notes

Reaction equation

HRID 1863936 reaction equation
Br.Br[C:3]1[N:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=[C:7]2[CH:6]=[N:5][CH:4]=1.O.[NH2:17][NH2:18]>C(O)C>[NH:17]([C:6]1[C:7]2[N:8]([N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:11]=2)[CH:3]=[CH:4][N:5]=1)[NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86614846HCID 86614846, compound

Product 1

HCID 57973794HCID 57973794, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 400 mg (1.15 mmol) of 5-bromo-2-(trifluoromethyl) [1,2,4]triazolo[1,5-a]pyrazine hydrobromide in 2.5 mL of dry ethanol was treated dropwise with 0.799 mL (11.5 mmol) of hydrazine hydrate, and stirring was continued at ambient temperature overnight. The reaction mixture was concentrated to dryness, and the residue was extracted with dichloromethane and then with tetrahydrofuran. The organic extracts were washed with saturated sodium bicarbonate aqueous solution, filtered, and concentrated. Purification of the residue by preparative HPLC (C18 reverse phase column, 10-60% acetonitrile in water containing 0.05% trifluoroacetic acid) afforded the title compound as a yellow solid. LC-MS 219 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionthe residue was extracted with dichloromethane
  3. washThe organic extracts were washed with saturated sodium bicarbonate aqueous solution
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by preparative HPLC (C18 reverse phase column, 10-60% acetonitrile in water containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-78adfffd80084326bb4f93ece1b66227
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

Loading…