Pyridine → HCID 23069568, Verbindung

HRID 853506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853506
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([NH2:25])[CH:19]=1)=[O:4].[N:26]1[CH:31]=C[CH:29]=[CH:28][CH:27]=1.ClC(OC1C=CC=CC=1)=[O:34].C1(N)CC1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([NH:25][C:31]([NH:26][CH:27]2[CH2:29][CH2:28]2)=[O:34])[CH:19]=1)=[O:4]

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 69828CyclopropylamineHCID 22936471HCID 22936471, Verbindung

Produkt 1

HCID 23069568HCID 23069568, VerbindungAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving N6-methyl-4-(3-amino-4-chlorophenoxy)-7-methoxy-6-quinolinecarboxamide (179 mg, 0.50 mmol) in dimethylformamide (2 ml) under a nitrogen atmosphere, pyridine (0.061 ml, 0.75 mmol) and phenyl chloroformate (0.094 ml, 0.75 mmol) were added dropwise at room temperature and the mixture was stirred for 1 hour. Cyclopropylamine (0.2 ml) was added dropwise and the mixture was further stirred overnight. The reaction solution was distributed between ethyl acetate and water, washed with saturated brine and dried over anhydrous sodium sulfate. After distilling off the solvent, the crystals precipitated from ethyl acetate were filtered out and blow-dried to obtain the title compound (163.9mg, 0.372 mmol, 74.3%) as white crystals.

Aufarbeitung

  1. waitthe mixture was further stirred overnight
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe crystals precipitated from ethyl acetate
  6. filtrationwere filtered out and
  7. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-949c6fb8169e468e8c02b7aab5837594
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253286B2

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