Hydrogen Bromide → 4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-hydroxy-N-[(6-methyl-pyridin-3-yl)methyl]benzamide

HRID 1784012Notes

Reaction equation

HRID 1784012 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:29]=[CH:28][C:16]([C:17]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=2)=[O:18])=[C:15]([O:30]C)[CH:14]=1.Br.C([O-])(O)=O.[Na+]>CC(O)C.O>[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:12][C:13]2[CH:29]=[CH:28][C:16]([C:17]([NH:19][CH2:20][C:21]3[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[O:18])=[C:15]([OH:30])[CH:14]=2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineHCID 575900544-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide

Product 1

HCID 866196654-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-hydroxy-N-[(6-methyl-pyridin-3-yl)methyl]benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (285 mg, 1.03 mmol) and 4-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide (280 mg, 1.03 mmol) are stirred in iPrOH (5 mL) and HBr (48% aq., 380 μL) is added. The mixture is heated at reflux for 24 hours. The cooled suspension is poured into NaHCO3 (sat. aq., 25 mL) and water (25 mL) and extracted with CHCl3 (4×30 mL). The extracts are dried over MgSO4 and evaporated. The residue is purified by column chromatography, eluting with 10% CH2Cl2/MeOH. The product-containing fractions are evaporated and the residue is triturated with MeOH to afford the title compound as a brown solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. extractionextracted with CHCl3 (4×30 mL)
  4. dry with materialThe extracts are dried over MgSO4
  5. customevaporated
  6. customThe residue is purified by column chromatography
  7. washeluting with 10% CH2Cl2/MeOH
  8. customThe product-containing fractions are evaporated
  9. customthe residue is triturated with MeOH

Sources & evidence

ORD record
ord-3e583b69311444e6ac7f180eec252c3a
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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