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Hydrochloric Acid → 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.HCl

HRID 613277
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 613277
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([Cl:16])=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH4+].[OH-].Cl>C(Cl)Cl.O.CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:25][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[ClH:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 14923Ammonium HydroxideHCID 195922341-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Produkt 1

HCID 700874611-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.HClAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b] quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and benzylamine (0.98 ml, 9 mmol) was heated at 80° C. overnight. The reaction mixture was poured into water (100 ml), then NH4OH (0.5 ml) was added. The mixture was extracted with CH2Cl2 (200 ml) and the CH2Cl2 was concentrated to about 20 ml and then this solution was purified by column chromatography on silica gel, followed by high pressure liquid chromatography eluting with 20% ethyl acetate/hexane to afford the product as the free base. The free base was dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl. The mixture was evaporated and the residue was crystallized from ether to afford 0.9 g of 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine·HCl, as an off white solid, m.p. 228-231° C.

Aufarbeitung

  1. extractionThe mixture was extracted with CH2Cl2 (200 ml)
  2. concentrationthe CH2Cl2 was concentrated to about 20 ml
  3. customthis solution was purified by column chromatography on silica gel
  4. washeluting with 20% ethyl acetate/hexane
  5. customto afford the product as the free base
  6. customThe mixture was evaporated
  7. customthe residue was crystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-9a7d3f81d303490bad8a0f632ae59596
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06008226

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