Triethylamine → HCID 69114052, compound

HRID 2053038Notes

Reaction equation

HRID 2053038 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:5]=[C:6]([C:8]([O:10]CC)=[O:9])[CH:7]=1.[O:18]1[CH:20]2[CH2:21][C:22]3[C:27]([CH:19]12)=[CH:26][CH:25]=[CH:24][CH:23]=3.C(N(CC)CC)C.C(OCC)(=O)C>CO.O>[OH:18][C@@H:20]1[CH2:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:19]1[O:1][C:2]1[C:3]2[N:4]([C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=2)[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 92838Indene oxideHCID 17954319HCID 17954319, compound

Product 1

HCID 69114052HCID 69114052, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 7.3 g (31.2 mmol) ethyl 8-hydroxy-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylate and 7.3 g (55.2 mmol) 1,2-epoxyindane in 150 ml methanol and 15 ml water are added 8.8 ml triethylamine and the reaction mixture is heated to 50° C. for 20 h. After cooling down, 100 ml ethyl acetate are added and the precipitate is collected by filtration. A second crop of material crystallizes from the mother liquor on evaporation. The total amount of precipitate is 6.0 g, which is suspended in a mixture of 100 ml dioxane and 60 ml 2N aqueous sodium hydroxide. After boiling under reflux for 1 h, the reaction mixture is evaporated to ⅓ of its volume and diluted with 15 ml methanol. The flask is placed in an ice bath and the pH is adjusted to pH=7 by adding 6N hydrochloric acid. After 30 min, the thick suspension is diluted with 20 ml methanol and filtered by suction. A second crop of material is obtained by evaporation of the mother liquor. The total amount of crude product is 6.75 g. Further purification is achieved by filtration over silica gel using dichloromethane:methanol:acetic acid (13:1:0.2) as eluent. Crystallization from methanol/diethyl ether yields 2.3 g (22%) of the title compound as a colourless solid (m.p. 229-231° C.).

Workup

  1. temperatureAfter cooling down
  2. filtrationthe precipitate is collected by filtration
  3. customA second crop of material crystallizes from the mother liquor on evaporation
  4. additionis suspended in a mixture of 100 ml dioxane and 60 ml 2N aqueous sodium hydroxide
  5. temperatureunder reflux for 1 h
  6. customthe reaction mixture is evaporated
  7. additiondiluted with 15 ml methanol
  8. customThe flask is placed in an ice bath
  9. additionby adding 6N hydrochloric acid
  10. additionthe thick suspension is diluted with 20 ml methanol
  11. filtrationfiltered by suction
  12. customA second crop of material is obtained by evaporation of the mother liquor
  13. customFurther purification
  14. filtrationis achieved by filtration over silica gel
  15. customCrystallization from methanol/diethyl ether

Sources & evidence

ORD record
ord-0dd8764887ae4c27892d681390bbab33
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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