Water → HCID 23158275, compound

HRID 601678Notes

Reaction equation

HRID 601678 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[CH:7]=1.Cl.[CH3:15][O:16][NH:17][CH3:18].Cl.CN(C)CCCN=C=NCC.O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11](=[O:13])[N:17]([O:16][CH3:15])[CH3:18])[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27570186-bromoimidazo[1,2-a]pyridine-2-carboxylic acid

Product 1

HCID 23158275HCID 23158275, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

850 mg of 6-bromo-2-hydroxycarbonyl-imidazo[1,2-a]pyridine, 519 mg of N-methoxy-N-methyl-amine hydrochloride, and 1.12 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were dissolved in 10 ml of pyridine, and the mixture was stirred at room temperature for 2 days. Water was added to the obtained solution, and the products were extracted with ethyl acetate. Organic layer was washed with saturated sodium chloride aqueous solution, and dried with anhydrous magnesium sulfate. Then, the solvents were distilled outunder reduced pressure. The obtained residues were purified by silicagel column chromatography (ethyl acetate) to obtain 362 mg of the above compound.

Workup

  1. extractionthe products were extracted with ethyl acetate
  2. washOrganic layer was washed with saturated sodium chloride aqueous solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThen, the solvents were distilled outunder reduced pressure
  5. customThe obtained residues were purified by silicagel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-2fb6a568fa9449d09a2fc8f2d2fa2726
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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