Hydrogen Bromide → HCID 57589970, compound

HRID 605996Notes

Reaction equation

HRID 605996 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].Br>C(O)CC>[CH2:19]([O:18][C:16](=[O:17])[C:15]1[CH:21]=[CH:22][CH:23]=[C:13]([NH:12][C:5]2[C:6]3[N:7]([N:8]=[CH:9][N:10]=3)[C:2]([Br:1])=[CH:3][N:4]=2)[CH:14]=1)[CH3:20]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11400Ethyl 3-aminobenzoateHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazine

Product 1

HCID 57589970HCID 57589970, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
85 °C

Procedure

5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (1.39 g, 5.00 mmol) and ethyl 3-aminobenzoate (0.93 g, 5.60 mmol) are stirred in PrOH (10 mL) and HBr (48% aq., 1.14 mL, 10 mmol) is added. The mixture is heated at 85° C. for 4 h and then cooled to rt and quenched with NaHCO3 (sat. aq., 25 mL). The resulting suspension is cooled to 0° C. and the white solid is collected by suction filtration and washed with water (10 mL). The crude product is taken up in EtOH and the solvent evaporated to afford the title compound as an off-white solid (1.79 g, 4.9 mmol) which is used without further purification.

Workup

  1. temperaturecooled to rt
  2. customquenched with NaHCO3 (sat. aq., 25 mL)
  3. temperatureThe resulting suspension is cooled to 0° C.
  4. filtrationthe white solid is collected by suction filtration
  5. washwashed with water (10 mL)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-b372c58024844f5dbed721d5ff016674
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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