Diethylamine → N-(4-((6-Cyano-7-(((2R)-3-(diethylamino)-2-hydroxypropyl)oxy)-4-quinolyl)oxy)phenyl)-N'-(4-fluorophenyl)urea

HRID 1433570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433570
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][C@H:15]1[CH2:17][O:16]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:27])=[CH:21][CH:20]=1)#[N:2].[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][C@H:15]([OH:16])[CH2:17][N:38]([CH2:39][CH3:40])[CH2:36][CH3:37])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)=[O:27])=[CH:21][CH:20]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 8021DiethylamineHCID 86591469HCID 86591469, Verbindung

Produkt 1

HCID 11533989N-(4-((6-Cyano-7-(((2R)-3-(diethylamino)-2-hydroxypropyl)oxy)-4-quinolyl)oxy)phenyl)-N'-(4-fluorophenyl)ureaAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

After dissolving N-(4-(6-cyano-7-((2R)-oxiran-2-yl)methoxy-4-quinolyl)oxyphenyl)-N′-(4-fluorophenyl)urea (200 mg, 0.425 mmol) in tetrahydrofuran (5.0 ml) under a nitrogen atmosphere, diethylamine (1.0 ml) was added and the mixture was stirred overnight at 60° C. The reaction solution was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography (eluent—ethyl acetate:methanol=9:1), the fraction containing the target substance was concentrated, methanol (5 ml) was added for crystallization, and the crystals were filtered out and blow-dried to obtain the title compound (126.4 mg, 0.233 mmol, 54.7%) as light yellow crystals.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe fraction containing the target substance
  3. concentrationwas concentrated
  4. additionmethanol (5 ml) was added for crystallization
  5. filtrationthe crystals were filtered out and
  6. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-72fecd87790b48e2a77c89245a7dfd72
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612092B2

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