Chloride → HCID 22672612, compound

HRID 1006667Notes

Reaction equation

HRID 1006667 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([CH3:24])[C:5]([CH2:6][NH:7][C:8]2[C:9]3[N:10]([C:15](C(O)=O)=[C:16]([CH3:18])[N:17]=3)[CH:11]=[C:12]([CH3:14])[CH:13]=2)=[C:4]([CH3:25])[CH:3]=1.C1(OC2C=CC=CC=2)C=CC=CC=1.[Cl-]>C(OCC)C>[CH3:18][C:16]1[N:17]=[C:9]2[C:8]([NH:7][CH2:6][C:5]3[C:4]([CH3:25])=[CH:3][C:2]([F:1])=[CH:23][C:22]=3[CH3:24])=[CH:13][C:12]([CH3:14])=[CH:11][N:10]2[CH:15]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 7583Diphenyl EtherHCID 22672636HCID 22672636, compound

Product 1

HCID 22672612HCID 22672612, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8-(4-fluoro-2,6-dimethylbenzylamino)-2-methyl-6-methylimidazo[1,2-a]pyridine 3-carboxylic acid (0.35 g, 1.03 mmol) and diphenyl ether and refluxed for 10 min. Petroleum ether 40-60 was added at room temperature followed by hydrogene chloride in diethyl ether. The petroleum ether diphenlether layer was removed from the formed precipitate. The precipitate was washed with petroleum ether thereafter dissolved in methylene chloride and basified with sodium hydroxide (2M). The layers were separated and the organic layer was washed with water. The solvent was evaporated and the residue was chromatographed (hexane:ethyl acetate, 2:1) giving 0.17 g (50%) of the title compound.

Workup

  1. temperaturerefluxed for 10 min
  2. customwas removed from the formed precipitate
  3. washThe precipitate was washed with petroleum ether
  4. dissolutionthereafter dissolved in methylene chloride
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. customThe solvent was evaporated
  8. customthe residue was chromatographed (hexane:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-abe3479f597340f3b264c1429d264ef4
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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