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Hydrochloric Acid → 6-Methyl-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine

HRID 541903
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Reaktionsgleichung

Reaktionsgleichung von HRID 541903
Cl.Cl.Cl.[NH2:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][C:13]2[CH:18]=[C:17]([NH:19][C:20]3[C:25]([CH3:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=3)[CH:16]=[CH:15][C:14]=2[NH2:28])[CH:8]=[CH:9][CH:10]=1.Cl.O.[OH-].[Na+]>COCCO.O1CCOCC1>[CH3:26][C:25]1[CH:24]=[N:23][C:22]2[NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([CH:6]=3)[CH2:11][CH2:12][C:13]3[CH:18]=[C:17]([NH:19][C:20]=1[N:21]=2)[CH:16]=[CH:15][C:14]=3[NH2:28]
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 866362872-[2-(3-Aminophenyl)ethyl]-N(4)-(2-chloro-5-methylpyrimidin-4-yl)benzene-1,4-diamine Trihydrochloride

Produkt 1

HCID 579623606-Methyl-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80192-MethoxyethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 2-[2-(3-aminophenyl)ethyl]-N(4)-(2-chloro-5-methylpyrimidin-4-yl)benzene-1,4-diamine trihydrochloride (0.16 g, 0.45 mmol) in 2-methoxyethanol (2 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (110 μL). The resultant mixture was heated at 150° C. in the microwave for 15 min. After cooling, water and NaOH (12 N) were added to neutralize the mixture to pH=7. The aqueous layer was extracted with EtOAc four times. The combined organic layers were dried, filtered and concentrated. The residue was purified by silica gel column chromatography to give the desired product as an off-white powder (60 mg, 48%). LCMS for C19H20N5 (M+H)+: m/z=318.2.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe aqueous layer was extracted with EtOAc four times
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f09dd5814fb240b18709d1864b890720
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871753B2

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