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Ethanol → (R)-N4-(3-Chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy)quinazoline-4,6-diamine

HRID 2042962
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2042962
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][C@@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(O)C.O>[Fe].C(O)(=O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:23][C@@H:24]1[CH2:28][CH2:27][O:26][CH2:25]1)[N:13]=[CH:12][N:11]=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 702EthanolHCID 962WaterHCID 66936816(R)-N-(3-Chloro-4-fluorophenyl)-6-nitro-7-((tetrahydrofuran-3-yl)oxy)quinazolin-4-amine

Produkt 1

HCID 66936486(R)-N4-(3-Chloro-4-fluorophenyl)-7-((tetrahydrofuran-3-yl)oxy)quinazoline-4,6-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator
HCID 176
Acetic Acid
Lösungsmittel

Versuchsvorschrift

A mixture of 12.80 g of 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-((R)-tetrahydrofuran-3-yloxy)quinazoline, 200 ml of ethanol, 100 ml of water, and 17.20 ml of glacial acetic acid is heated to reflux temperature. Then a total of 7.00 g of iron powder is added in batches. The reaction mixture is refluxed for about four hours and then cooled to ambient temperature overnight. For working up, the reaction mixture is evaporated using the rotary evaporator. The residue is taken up in methylene chloride/methanol (9:1), mixed with 20 ml of concentrated ammonia solution and filtered through a layer of silica gel. It is washed with copious amounts of methylene chloride/methanol (9:1) and the combined filtrates are evaporated down. The residue is stirred with diethylether and suction filtered. Yield: 8.59 g (73% of theory); mass spectrum (ESI−): m/z=373, 375 [M−H]−; Rf value: 0.27 (silica gel, ethyl acetate/methanol=9:1).

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux temperature
  3. temperatureThe reaction mixture is refluxed for about four hours
  4. customthe reaction mixture is evaporated
  5. customthe rotary evaporator
  6. additionmixed with 20 ml of concentrated ammonia solution
  7. filtrationfiltered through a layer of silica gel
  8. washIt is washed with copious amounts of methylene chloride/methanol (9:1)
  9. customthe combined filtrates are evaporated down
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-294b76dd278144afb8ccd507ac564958
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586608B2

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