Ethanol → HCID 70115249, compound

HRID 467710Notes

Reaction equation

HRID 467710 reaction equation
Cl.[NH2:2][C:3]1[C:8]([C:9]#N)=[CH:7][N:6]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=[C:5]2[CH:4]=1.[OH:20]S(O)(=O)=O.[CH3:25][CH2:26][OH:27]>O>[CH2:26]([O:27][C:9]([C:8]1[C:3]([NH2:2])=[CH:4][C:5]2[N:6]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH:7]=1)=[O:20])[CH3:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 70096399HCID 70096399, compound

Product 1

HCID 70115249HCID 70115249, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 7-amino-2-phenyl-imidazo[1,2-a]pyridine-6-carbonitrile hydrochloride (1.0 g, 3.7 mmol) at rt in EtOH (20 ml) under an argon atmosphere was added H2SO4 (1.5 ml, 27.7 mmol) in one portion. The mixture was heated to reflux and stirring was continued for 2 days. The mixture was cooled to rt and diluted with 10 ml H2O. The solid was collected by filtration, washed with H2O and dried. Then it was suspended in CH2Cl2/MeOH 9:1 and treated with triethylamine to give a yellow solution. The dissolved material was adsorbed on Isolute® Flash-NH2 silica gel (from Separtis) and purified by chromatographie on the same silica gel as stationary phase using a CH2Cl2/MeOH gradient as eluent, providing the title compound as off-white solid (642 mg, 62%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe solid was collected by filtration
  4. washwashed with H2O
  5. customdried
  6. additiontreated with triethylamine
  7. customto give a yellow solution
  8. custompurified by chromatographie on the same silica gel as stationary phase

Sources & evidence

ORD record
ord-57e25b0e06f24663862725d387ada143
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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