Sodium Iodide → Isopropyl 8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

HRID 2184309Notes

Reaction equation

HRID 2184309 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:14]([CH3:18])=[C:15]([CH3:17])[N:16]=2)[CH:5]=[C:6]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH:7]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[CH3:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:29]=1[CH2:30]Cl>C(O)(C)C.O>[CH3:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:29]=1[CH2:30][NH:1][C:2]1[C:3]2[N:4]([C:14]([CH3:18])=[C:15]([CH3:17])[N:16]=2)[CH:5]=[C:6]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2×HCID 2211542,6-Dimethylbenzyl Chloride2×HCID 9942912Isopropyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 11164436Isopropyl 8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylateYield 104.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent3×

Conditions

Temperature
70 °C

Procedure

Isopropyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (9.85 kg, 1.0 equiv., 29.71 mol) was suspended in isopropanol (59 L); NaI (0.6 equiv., 2.68 kg, 17.88 mol) and is K2CO3 (2.5 equiv, 10.29 kg, 74.48 mol) were added and the mixture was heated to about 70° C. 2,6-Dimethylbenzyl chloride (1.1 equiv, 5.22 kg, 32.77 mol) was dissolved in isopropanol (˜60 L) and this solution was added to the reaction mixture. After the addition was complete, the temperature was kept at 60° C. for additional 1.5 hours. Additional K2CO3 was added (9.15 kg) and the resulting suspension was stirred for further 2 h at 60° C. Additional 2,6-dimethylbenzyl chloride (2.76 kg) in isopropanol (22L) was added slowly at an temperature of 60° C.; after the addition the reaction mixture was stirred for further 4 hours at this temperature. The suspension was diluted with water (124L), cooled, stirred and filtered. The filtercake was washed with water and then with cold isopropanol, dried under reduced pressure at 40° C. to give 11.37 kg wet material, yield: 90%.

Workup

  1. additionwere added
  2. additionthis solution was added to the reaction mixture
  3. additionAfter the addition
  4. additionafter the addition the reaction mixture
  5. stirringwas stirred for further 4 hours at this temperature
  6. temperaturecooled
  7. stirringstirred
  8. filtrationfiltered
  9. washThe filtercake was washed with water
  10. dry with materialwith cold isopropanol, dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-2bd1aca8f9124db9b1267ce64a501d88
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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