2-Methoxyethylamine → N6-(2-Methoxyethyl)-4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino}phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxamide

HRID 1010247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010247
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[NH:27][C:28]([NH:30][CH:31]1[CH2:33][CH2:32]1)=[O:29])[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[C:13]([C:16]([OH:18])=O)[CH:14]=2)[N:9]=[CH:8][CH:7]=1.[CH3:34][O:35][CH2:36][CH2:37][NH2:38].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(OCC)(=O)C.O.CN(C)C=O>[CH3:34][O:35][CH2:36][CH2:37][NH:38][C:16]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:19][CH2:20][CH2:21][O:22][CH3:23])[N:9]=[CH:8][CH:7]=[C:6]2[O:5][C:4]1[CH:24]=[CH:25][C:26]([NH:27][C:28]([NH:30][CH:31]2[CH2:32][CH2:33]2)=[O:29])=[C:2]([Cl:1])[CH:3]=1)=[O:18]

Komponenten

8

Edukt 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 589311914-(3-Chloro-4-{[(cyclopropylamino)carbonyl]amino)phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylic acid

Produkt 1

HCID 58930857N6-(2-Methoxyethyl)-4-(3-chloro-4-{[(cyclopropylamino)carbonyl]amino}phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(3-Chloro-4-{[(cyclopropylamino)carbonyl]amino}phenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylic acid (200 mg), 2-methoxyethylamine (38 mg), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (Bop reagent) (230 mg), triethylamine (0.12 ml) and dimethylformamide (5 ml) were stirred together at room temperature for 14 hours. Water and ethyl acetate were added to the reaction solution for extraction, NH type silica gel was added to the extract, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (ethyl acetate). The solvent was distilled off under reduced pressure to obtain 120 mg of the target substance as a solid.

Aufarbeitung

  1. additionwas added to the extract
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with NH type silica gel, and column purification
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto obtain 120 mg of the target substance as a solid

Quellen und Nachweise

ORD-Eintrag
ord-c926d25070af46c08926328e9f3e3df9
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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