Hydrogen Bromide → HCID 57589970, compound

HRID 1784015Notes

Reaction equation

HRID 1784015 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>CC(O)C>[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 3776IsopropanolSolvent

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 iPrOH (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-5a9e8cf340204f16a39d32d54c680c26
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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