Ethanolamine → Linaprazan

HRID 1184638Notes

Reaction equation

HRID 1184638 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].N12CCCN=C1CCCCC2>CO>[CH3:21][C:19]1[N:20]=[C:7]2[C:6]([NH:5][CH2:4][C:3]3[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:2]=3[CH3:1])=[CH:11][C:10]([C:12]([NH:31][CH2:30][CH2:28][OH:29])=[O:13])=[CH:9][N:8]2[C:18]=1[CH3:22]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11164436Isopropyl 8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 9951066LinaprazanYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Isopropyl 8-[(2,6-dimethylbenzyl)amino]-2.3-dimethylimidazo[1,2-a]pyridine-6-carboxylate (obtained as described in WO2/20523) (5 g, 14 mmol), ethanolamine (2.0 g 33 mmol) and 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) 1.5 g, 10 mmol) were dissolved in methanol (25 ml). The mixture was refluxed over night. The reaction mixture was cooled to 5° C. The solid product was filtered off and washed with methanol (15 ml). 4.2 g (84%) of the title compound was obtained as a white solid. The structure of the compound was confirmed with 1H-NMR spectrum.

Workup

  1. temperatureThe mixture was refluxed over night
  2. filtrationThe solid product was filtered off
  3. washwashed with methanol (15 ml)

Sources & evidence

ORD record
ord-5b7069b11e5f4431893467402fb01dca
Source dataset
uspto-grants-2014_03
Patent number
US08669269B2

Reaction notes

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