Water → HCID 59295129, compound

HRID 2233034Notes

Reaction equation

HRID 2233034 reaction equation
[Cl:1][C:2]1[C:3]([NH:8][NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[N:4][CH:5]=[CH:6][N:7]=1.N1C=CC=CC=1.[Br:22]Br.O>CC(O)=O>[Br:22][C:6]1[N:7]=[C:2]([Cl:1])[C:3]([NH:8][NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14])=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24408BromineHCID 58446973HCID 58446973, compound

Product 1

HCID 59295129HCID 59295129, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2.40 g of the product of Step A and 1.97 g of pyridine in AcOH (10.0 mL) at 0° C. was stirred as a solution of 1.92 g of bromine in AcOH (1.0 mL) was added dropwise. The resulting mixture was stirred at 0° C. for one h and then warmed to ambient temperature and stirred for an additional 16 h. The reaction mixture was poured into water and extracted with EtOAc (2×). The combined organic extracts were washed with water, dried over magnesium sulfate, filtered, and concentrated to an oil that was purified by silica gel chromatography to provide trifluoroacetic acid N′-(5-bromo-3-chloro-pyrazin-2-yl)-hydrazide as a white solid. MS (M+H+)=320.1.

Workup

  1. additionwas added dropwise
  2. temperaturewarmed to ambient temperature
  3. stirringstirred for an additional 16 h
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil that
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-7c40a0dece594b1b8479acefcc7612d6
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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