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Lithium Hydroxide → 3-[4-(2-chloro-7-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochloride

HRID 1877810
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1877810
[ClH:1].Cl.[CH3:3][C:4]([CH3:16])([CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:5]([O:7]C)=[O:6].[Cl:17][C:18]1[CH:19]=[C:20]2[N:26]([CH:27]=1)[CH2:25][C:24]1[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:23]=1[N:22]=[C:21]2Cl.C(=O)(O)[O-].[Na+].[OH-].[Li+]>O.C(O)(=O)C.C(#N)C>[ClH:17].[ClH:1].[Cl:17][C:18]1[CH:19]=[C:20]2[N:26]([CH:27]=1)[CH2:25][C:24]1[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:23]=1[N:22]=[C:21]2[N:13]1[CH2:14][CH2:15][N:10]([CH2:9][C:4]([CH3:16])([CH3:3])[C:5]([OH:7])=[O:6])[CH2:11][CH2:12]1
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Komponenten

8

Edukt 4

HCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 68155933Methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate dihydrochlorideHCID 681560022,11-dichloro-7-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 681562783-[4-(2-chloro-7-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochloride
Ausbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Dissolve methyl 2,2-dimethyl-3-(piperazin-1-yl)-propanoate dihydrochloride (1.49 g, 5.47 mmoles) in water and absorb onto an SCX2 column. Wash the column with methanol and elute methyl 2,2-dimethyl-3-piperazin-1-yl-propanoate with 2M ammonia in methanol. Remove the methanol in vacuo and add the methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate to acetonitrile (12 mL). Add 2,11-dichloro-7-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.85 g, 3.22 mmoles) and sodium bicarbonate (0.405 g, 4.83 mmoles) to the acetonitrile solution. Heat and stir in the microwave for 30 minutes at 140° C. Cool to room temperature, absorb the reaction mixture onto silica and purify by chromatography (gradient elution with EtOAc/isohexane 0:100% to 100:0%). Collect the fractions containing product and evaporate the solvent in vacuo and dissolve the residue in methanol (10 mL) and add lithium hydroxide (0.235 g, 9.65 mmoles). Heat and stir the methanolic solution in the microwave for 12.5 minutes at 140° C. Cool to room temperature and acidify with acetic acid and then evaporate the solvent under reduced pressure. Dissolve the residue in excess 2M HCl (aq) and then evaporated to dryness. Dissolve the residue in water and immobilise onto a macroporous polystyrene hydrogen carbonate (PL-HCO3) resin. Wash the resin with water and elute from the resin with 2M HCl (aq). Evaporate the solution to dryness to give 3-[4-(2-chloro-7-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochloride (0.177 g; 11.28% yield). MS (m/z): 415.18 (M+1).

Aufarbeitung

  1. customabsorb onto an SCX2 column
  2. washWash the column with methanol
  3. washelute methyl 2,2-dimethyl-3-piperazin-1-yl-propanoate with 2M ammonia in methanol
  4. customRemove the methanol in vacuo
  5. additionadd the methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate to acetonitrile (12 mL)
  6. temperatureHeat
  7. temperatureCool to room temperature
  8. customabsorb the reaction mixture onto silica
  9. custompurify by chromatography (gradient elution with EtOAc/isohexane 0:100% to 100:0%)
  10. customCollect the fractions
  11. additioncontaining product
  12. customevaporate the solvent in vacuo
  13. dissolutiondissolve the residue in methanol (10 mL)
  14. temperatureHeat
  15. stirringstir the methanolic solution in the microwave for 12.5 minutes at 140° C
  16. temperatureCool to room temperature
  17. customevaporate the solvent under reduced pressure
  18. dissolutionDissolve the residue in excess 2M HCl (aq)
  19. customevaporated to dryness
  20. dissolutionDissolve the residue in water
  21. washWash the resin with water
  22. washelute from the resin with 2M HCl (aq)
  23. customEvaporate the solution to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1c06837dfcd4473a8230a9f45129f992
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08314092B2

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