Hydrogen Bromide → 4-(5-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-2-methoxy-N-(6-methylpyridin-3-ylmethyl)benzamide

HRID 1924962Notes

Reaction equation

HRID 1924962 reaction equation
[Br:1][C:2]1[N:7]2[CH: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][CH3:31])[CH:14]=1.Br.C([O-])(O)=O.[Na+]>CC(O)C.O>[Br:1][C:2]1[N:7]2[CH: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]([O:30][CH3:31])[CH:14]=2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazineHCID 575900544-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide

Product 1

HCID 590230284-(5-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-2-methoxy-N-(6-methylpyridin-3-ylmethyl)benzamideYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

5,8-dibromoimidazo[1,2-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 (3×40 mL). The extracts are dried over MgSO4 and evaporated. The residue is purified by column chromatography, eluting with 10%-20% DCM/MeOH to afford the title compound as a pale yellow solid (200 mg, 0.43 mmol).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. extractionextracted with CHCl3 (3×40 mL)
  4. dry with materialThe extracts are dried over MgSO4
  5. customevaporated
  6. customThe residue is purified by column chromatography
  7. washeluting with 10%-20% DCM/MeOH

Sources & evidence

ORD record
ord-633ff21f22354fd5b2401811a5e51949
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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