Triethylamine → N6-Methyl-4-(3-chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamide

HRID 853584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853584
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([C:16]([OH:18])=O)[CH:14]=2)[N:9]=[CH:8][CH:7]=1.CN.CO.[CH2:34]([N:36](CC)CC)C.F[P-](F)(F)(F)(F)F.CN([PH+](N(C)C)N(C)C)C>CN(C)C=O.O.C(OCC)(=O)C>[CH3:34][NH:36][C:16]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:19][CH3:20])[N:9]=[CH:8][CH:7]=[C:6]2[O:5][C:4]1[CH:21]=[CH:22][C:23]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[C:2]([Cl:1])[CH:3]=1)=[O:18]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 22494795Tris(dimethylamino)phosphonium hexafluorophosphateHCID 229369534-(3-Chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acidHCID 57454252Monomethylamine methanol

Produkt 1

HCID 11553718N6-Methyl-4-(3-chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving 4-(3-chloro-4-(((ethylamino)carbonyl) amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acid (104 mg, 0.250mmol) in dimethylformamide (3 ml), there were added a 40% methylamine-methanol solution (0.100 ml), triethylamine (0.250 ml) and 1H-1,2,3-benzotriazol-1-yloxy)(tri(dimethylamino)) phosphonium hexafluoro phosphate (221mg, 0.500mmol) in that order at room temperature, and the mixture was stirred for 15 hours. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was suspended in ethyl acetate, the suspension was diluted with hexane and the crystals were filtered out and blow-dried to obtain the title compound (79.0 mg, 0.184 mmol, 74%) as white crystals.

Aufarbeitung

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent
  4. additionthe suspension was diluted with hexane
  5. filtrationthe crystals were filtered out and
  6. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-ad9f08a5babf4aaea3a6e73be8be413d
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253286B2

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