Hydrochloric Acid → HCID 57878312, compound

HRID 656375Notes

Reaction equation

HRID 656375 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@:6]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[N:11]1[CH3:17])[CH2:5]2.F[B-](F)(F)F.F[B-](F)(F)F.CN([CH:31]=[C:32]([CH2:37][NH+](C)C)[CH2:33][NH+](C)C)C.Cl.C([O-])(O)=[O:43].[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl.C1COCC1>[CH3:17][N:11]1[C@@:6]2([CH2:7][C:8]3[CH:9]=[C:10]4[C:2](=[CH:3][C:4]=3[CH2:5]2)[N:1]=[CH:33][C:32]([CH:37]=[O:43])=[CH:31]4)[C:14](=[O:15])[NH:13][C:12]1=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57774196HCID 57774196, compound2×HCID 86634559HCID 86634559, compound

Product 1

HCID 57878312HCID 57878312, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)-5′-Amino-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione (0.500 g, 2.16 mmol, described in Intermediate 8) and 2-dimethylaminomethylene-1,3-bis(dimethylammonio)propane bis(tetrafluoroborate) (1.77 g, 4.97 mmol) were suspended in glacial acetic acid and the mixture was heated to reflux for 20 h. The mixture was allowed to cool to ambient temperature before the bulk of the acetic acid was removed in vacuo. THF (10 mL) and 1 N aqueous HCl (10 mL, 10 mmol) were added and the mixture was stirred at ambient temperature for 2.5 h. The mixture was then poured into a separatory funnel containing CHCl3 (150 mL) and saturated aqueous NaHCO3 (30 mL). The aqueous layer was extracted once with CHCl3 (100 mL) and the combined organics were dried over Na2SO4. Filtration to remove drying agent gave a solution which was concentrated in vacuo to give a yellow residue. The impure product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:1 to 94:6, to give the title compound. MS: m/z=296 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 h
  3. customwas removed in vacuo
  4. additionThe mixture was then poured into a separatory funnel
  5. extractionThe aqueous layer was extracted once with CHCl3 (100 mL)
  6. dry with materialthe combined organics were dried over Na2SO4
  7. filtrationFiltration
  8. customto remove
  9. customdrying agent
  10. customgave a solution which
  11. concentrationwas concentrated in vacuo
  12. customto give a yellow residue
  13. customThe impure product was purified by silica gel chromatography
  14. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-08102eb2532245caa96f65384b88adb8
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

Loading…