Ethanolamine → Linaprazan

HRID 2184310Notes

Reaction equation

HRID 2184310 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=2)[CH:9]=[C:10]([C:12](OC(C)C)=[O:13])[CH:11]=1.[CH2:28]([CH2:30][NH2:31])[OH:29]>C1COCC1>[CH3:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:2]([CH3:1])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=2)[CH:9]=[C:10]([C:12]([NH:31][CH2:30][CH2:28][OH:29])=[O:13])[CH:11]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 11164436Isopropyl 8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 9951066Linaprazan

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A reactor was charged with isopropyl 8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (11.30 kg, 1 equiv., 27.02 mol) and THF (45 L), ethanolamine (18.97 kg, 11 equiv., 309.2 mol) was added at about 20° C. The suspension was heated to about 100° C. Some solvent was distilled off and then THF (35L) was added and the distillation was continued. The procedure of adding THF and distilling it off was repeated until complete conversion. To the suspension ethanol (140L) was added and the suspension was heated to reflux. To obtain a clear solution additional ethanol (13L) was added. The hot solution was filtered and then cooled. The white solid was filtered off, washed with ethanol and dried to yield the product as a white powder. (8271 g).

Workup

  1. additionwas added at about 20° C
  2. distillationSome solvent was distilled off
  3. additionTHF (35L) was added
  4. distillationthe distillation
  5. distillationThe procedure of adding THF and distilling it
  6. additionTo the suspension ethanol (140L) was added
  7. temperaturethe suspension was heated to reflux
  8. customTo obtain a clear solution additional ethanol (13L)
  9. additionwas added
  10. filtrationThe hot solution was filtered
  11. temperaturecooled
  12. filtrationThe white solid was filtered off
  13. washwashed with ethanol
  14. customdried

Sources & evidence

ORD record
ord-676336f62eb247379ba799de5f10eeac
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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