StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → 1-ethyl-6-nitro-N-(3-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586173
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1586173
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=3)[CH3:2].C(N(CC)CC)C.[OH:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH:30]([CH2:34][NH2:35])[CH2:29]1.[NH4+].[OH-]>C1COCC1.CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:35][CH2:34][CH:30]4[CH2:31][CH2:32][CH2:33][CH:28]([OH:27])[CH2:29]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=3)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 212177131-ethyl-4-chloro-6-nitro-1H-pyrazolo[3,4-b]quinolineHCID 230098443-(Aminomethyl)cyclohexan-1-ol

Produkt 1

HCID 212177071-ethyl-6-nitro-N-(3-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

and (b) A mixture of 1-ethyl-6-nitro-4-chloro-1H-pyrazolo[3,4-b]quinoline (2.7 g, 17.8 mmol), triethylamine (3 ml, 0.02 mol), DMSO (15 ml) and 3-hydroxycyclohexylmethylamine (4.97 g, 18 mmol) is heated at 110° C. overnight. The reaction mixture is poured into ice water (200 ml)/NH4OH (10 ml) and the solid which forms is collected by filtration. The filtrate is then extracted with CH2Cl2 (2×100 ml). The solid is stirred and sonicated with CH2Cl2 (2×200 ml), and any solids which did not go into solution are collected by filtration. All of the above CH2Cl2 filtrates and extracts are combined, washed with water and evaporated. The residue is slurried with ethyl acetate (10-15 ml)/ether (20 ml) and a red colored solid is collected by filtration and washed with ether. The solid is purified by column chromatography (2×) on silica gel (note that the solid is preloaded onto 50-100 g of silica gel) eluting with 40% THF/cyclohexane and each of the diastereomers which is isolated is dissolved in hot THF, filtered and the solvent is evaporated. Each of the residues is slurried with ethanol (5 ml), filtered and dried to afford 0.69 g of 1-ethyl-6-nitro-N-(3-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (the RS,SR diastereomer which is labelled as Example 36(a)), m.p. 236°-238° C. and 2.23 g of 1-ethyl-6-nitro-N-(3-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (the RR,SS diastereomer which is labelled as Example 36(b)), m.p. 247°-248° C.

Aufarbeitung

  1. filtrationthe solid which forms is collected by filtration
  2. extractionThe filtrate is then extracted with CH2Cl2 (2×100 ml)
  3. customsonicated with CH2Cl2 (2×200 ml)
  4. filtrationare collected by filtration
  5. washwashed with water
  6. customevaporated
  7. filtrationa red colored solid is collected by filtration
  8. washwashed with ether
  9. customThe solid is purified by column chromatography (2×) on silica gel (note that the solid
  10. washeluting with 40% THF/cyclohexane
  11. customeach of the diastereomers which is isolated
  12. filtrationfiltered
  13. customthe solvent is evaporated
  14. filtrationfiltered
  15. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3541c97a307f40ee9823f5a21136d912
Quelldatensatz
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05942520

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion