Water → N,N-diethyl-3-iodo-2-isopropylimidazo[1,2-a]pyridine-7-carboxamide

HRID 1468262Notes

Reaction equation

HRID 1468262 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]2[CH:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][N:7]2[CH:15]=1)([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.[CH2:39]([NH:41][CH2:42][CH3:43])[CH3:40].[I:44]N1C(=O)CCC1=O>CN(C=O)C>[CH2:39]([N:41]([CH2:42][CH3:43])[C:12]([C:10]1[CH:9]=[CH:8][N:7]2[C:15]([I:44])=[C:4]([CH:1]([CH3:2])[CH3:3])[N:5]=[C:6]2[CH:11]=1)=[O:14])[CH3:40]

Participants

8

Reactant 6

HCID 962WaterHCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 120273N-IodosuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 643960682-(Propan-2-yl)imidazo[1,2-a]pyridine-7-carboxylic acid

Product 1

HCID 86710021N,N-diethyl-3-iodo-2-isopropylimidazo[1,2-a]pyridine-7-carboxamideYield 113%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Isopropylimidazo[1,2-a]pyridine-7-carboxylic acid (3.00 g, 14.7 mmol) obtained in step 2 was dissolved in DMF (15 mL), and the solution was stirred at 60° C. for 2 hours after adding EDC.HCl (4.20 g, 22.0 mmol), HOBt.H2O (3.00 g, 22.0 mmol), and diethylamine (2.70 mL, 29.4 mmol). The reaction mixture was extracted with ethyl acetate after adding a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with a saturated ammonium chloride aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was dissolved in DMF (20 mL), and stirred under light shielding at room temperature for 1 hour after adding N-iodosuccinimide (4.20 g, 18.5 mmol). The reaction mixture was extracted with ethyl acetate after adding a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was slurried with heptane. The resulting crystals were collected by filteration, and dried to give N,N-diethyl-3-iodo-2-isopropylimidazo[1,2-a]pyridine-7-carboxamide (6.40 g, yield 99%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. additionafter adding a saturated sodium hydrogen carbonate aqueous solution
  3. washThe organic layer was washed with a saturated ammonium chloride aqueous solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then evaporated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in DMF (20 mL)
  7. stirringstirred under light
  8. waitshielding at room temperature for 1 hour
  9. extractionThe reaction mixture was extracted with ethyl acetate
  10. additionafter adding a saturated sodium hydrogen carbonate aqueous solution
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was then evaporated under reduced pressure
  14. customThe resulting crystals were collected by filteration
  15. customdried

Sources & evidence

ORD record
ord-dfcf4b9850a845928e9983c5c195d244
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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