Ethanolamine → Linaprazan

HRID 427483Notes

Reaction equation

HRID 427483 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][C:7]([C:20](OC)=[O:21])=[CH:6][N:5]2[C:24]=1[CH3:25].[CH2:26]([CH2:28][NH2:29])[OH:27].[C-]#N.[Na+]>C(COC)OC>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][C:7]([C:20]([NH:29][CH2:28][CH2:26][OH:27])=[O:21])=[CH:6][N:5]2[C:24]=1[CH3:25]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8929Sodium CyanideHCID 12148917Methyl 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 9951066LinaprazanYield 85.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate (0.12 g, 0.33 mmol), ethanolamine (0.2 g, 3.3 mmol) and sodium cyanide (10 mg, 0.2 mmol) were refluxed in dimethoxyethane (2 ml) for 20 h. The solvent was evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride:methanol (92:8) as eluent gave the product which was washed with diethyl ether to give 103 mg (79%) of the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customPurification of the residue by column chromatography on silica gel
  3. customgave the product which
  4. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-ea41d08cadc743968576b598892ee8a3
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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