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Potassium Hydroxide → HCID 71240555, Verbindung

HRID 80774
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 80774
Cl[C:2]1[C:3]2[CH2:31][N:30]([C:32]3[CH:37]=[C:36]([CH:38]([CH3:40])[CH3:39])[CH:35]=[CH:34][C:33]=3[CH3:41])[CH2:29][CH2:28][C:4]=2[N:5]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[C:10]([CH3:27])=[CH:11][N:12]3[S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[N:7]=1.[CH3:42][O-:43].[Na+].[OH-].[K+].[OH-].[NH4+]>CO.CCOC(C)=O.O.ClCCl.[Cl-].[Na+].O>[CH:38]([C:36]1[CH:35]=[CH:34][C:33]([CH3:41])=[C:32]([N:30]2[CH2:29][CH2:28][C:4]3[N:5]=[C:6]([C:8]4[CH:16]=[CH:15][CH:14]=[C:13]5[C:9]=4[C:10]([CH3:27])=[CH:11][N:12]5[S:17]([C:20]4[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=4)(=[O:18])=[O:19])[N:7]=[C:2]([O:43][CH3:42])[C:3]=3[CH2:31]2)[CH:37]=1)([CH3:40])[CH3:39]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 10942334Sodium MethoxideHCID 866902544-chloro-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Produkt 1

HCID 71240555HCID 71240555, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, prepared as described in Example 17 (110 mg, 0.188 mmol) in methanol (5 mL) was added 25% sodium methoxide in methanol (40.6 mg, 0.188 mmol). The reaction was stirred for ca. 40 minutes at room temperature at which time the mixture was diluted with EtOAc and water. The layers were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting residue was added to a microwave vial, and diluted with EtOH (2 mL) and charged with KOH (ca. 100 mg, 1.75 mmol) and 28% ammonium hydroxide in water (1 mL, 7.25 mmol). The vial was sealed and heated via microwave irradiation at 100° C. for 45 minutes. The reaction mixture was cooled to room temperature and diluted with dichloromethane and brine. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (0-100% ethyl acetate/heptanes) and then further purified by reverse phase HPLC (20-100% MeCN/0.1% NH4OH in water to afford 6-(5-isopropyl-2-methylphenyl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine.

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe resulting residue was added to a microwave vial
  7. additiondiluted with EtOH (2 mL)
  8. customThe vial was sealed
  9. temperatureheated via microwave irradiation at 100° C. for 45 minutes
  10. temperatureThe reaction mixture was cooled to room temperature
  11. customThe layers were separated
  12. extractionthe aqueous layer was extracted two additional times with dichloromethane
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customThe resulting residue was purified by silica gel flash chromatography (0-100% ethyl acetate/heptanes)
  17. customfurther purified by reverse phase HPLC (20-100% MeCN/0.1% NH4OH in water

Quellen und Nachweise

ORD-Eintrag
ord-0a516fe914244675bf442490cb4ddd12
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846656B2

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