1,1'-Carbonyldiimidazole → HCID 67293127, compound

HRID 1025546Notes

Reaction equation

HRID 1025546 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.N1(C(N2C=CN=C2)=O)C=CN=C1.Cl.[F:28][C:29]1[CH:38]=[C:37]2[C:32]([CH2:33][CH2:34][CH2:35][NH:36]2)=[CH:31][CH:30]=1>C1COCC1>[F:28][C:29]1[CH:38]=[C:37]2[C:32]([CH2:33][CH2:34][CH2:35][N:36]2[C:12]([C:3]2[C:2]([OH:1])=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[N:10]3)=[CH:5][CH:4]=2)=[O:14])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 552120741224640-26-9

Product 1

HCID 67293127HCID 67293127, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-hydroxyquinoline-7-carboxylic acid (100 mg, 0.53 mmol) and di(1H-imidazol-1-yl)methanone (86 mg, 0.53 mmol) in THF (6 mL) was heated to reflux for 4 h, under nitrogen. The reaction mixture was allowed to cool to RT and 7-fluoro-1,2,3,4-tetrahydroquinoline hydrochloride (84.4 mg, 0.45 mmol) and TEA (0.062 mL, 0.45 mmol) were added. The resulting mixture was heated in a MW oven at 120° C. for 90 min and then at 140° C. for 2 h. The reaction mixture was then quenched with H2O and an aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC. Product-containing fractions were combined, made basic with a saturated aqueous solution of sodium hydrogen carbonate and CH3CN was removed under reduced pressure. The aqueous phase was extracted with DCM and the separated organics dried over Na2SO4, filtered and concentrated to dryness, affording the title compound (19 mg, 0.06 mmol) as a off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h, under nitrogen
  3. temperatureThe resulting mixture was heated in a MW oven at 120° C. for 90 min
  4. customThe reaction mixture was then quenched with H2O
  5. extractionan aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM
  6. dry with materialThe separated organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative HPLC
  10. customwas removed under reduced pressure
  11. extractionThe aqueous phase was extracted with DCM
  12. dry with materialthe separated organics dried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0cfef7f8bce04a838ca3ccdea869d94d
Source dataset
uspto-grants-2014_05
Patent number
US08729098B2

Reaction notes

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