Sodium Iodide → Pumaprazole

HRID 1377475Notes

Reaction equation

HRID 1377475 reaction equation
[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[NH2:9][C:10]1[C:11]2[N:12]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1.[CH3:21][O:22][C:23]([NH:25][C:26]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:27]=1[CH2:28]Cl)=[O:24]>CC(C)=O.O>[CH3:21][O:22][C:23]([NH:25][C:26]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:27]=1[CH2:28][NH:9][C:10]1[C:11]2[N:12]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)=[O:24]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 143684802-Methyl-6-methoxycarbonylaminobenzyl chlorideHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amine

Product 1

HCID 3052764PumaprazoleYield 56%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4.5 g of sodium iodide and 6.63 g of dry sodium carbonate are added to a solution of 4.03 g of 8-amino-2,3-dimethylimidazo[1,2-a]pyridine and 6.41 g of 2-methoxycarbonylamino-6-methyl-benzyl chloride in 400 ml of dry acetone, and the mixture is heated under reflux for 6 h. After cooling to RT, 400 ml of water are added and the acetone is distilled off in a water jet vacuum. The aqueous residue is then extracted three times with each time 200 ml of ethyl acetate. The combined organic extracts are washed with 300 ml of water, dried over magnesium sulfate and then concentrated. The residue is purified by chromatography on silica gel (toluene/dioxan=9:1 as eluent). The fractions with Rf =0.2 are concentrated and then recrystallized from diisopropyl ether. 4.71 g (56%) of the title compound of m.p. 136°-138° C. are isolated.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 h
  3. distillationthe acetone is distilled off in a water jet vacuum
  4. extractionThe aqueous residue is then extracted three times with each time 200 ml of ethyl acetate
  5. washThe combined organic extracts are washed with 300 ml of water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography on silica gel (toluene/dioxan=9:1 as eluent)
  9. concentrationThe fractions with Rf =0.2 are concentrated
  10. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-0707fd957aa4460888e2a87a0f774460
Source dataset
uspto-grants-1997_09
Patent number
US05665730

Reaction notes

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