Hydrochloric Acid → HCID 22672612, compound

HRID 1369563Notes

Reaction equation

HRID 1369563 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 313Hydrochloric AcidHCID 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 hydrogen 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-236ace61b1e4465c9d10a5b3153375f7
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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