N1-[3-Fluoro-4-[[6-methoxy-7-(phenylmethoxy)-4-quinolinyl]oxy]phenyl]-N2-(2-phenylethyl)ethanediamide → HCID 136168658, Verbindung

HRID 563001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563001
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:39])[C:28]([NH:30][CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:29])=[CH:22][C:21]=3[F:40])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:41][CH3:42])C1C=CC=CC=1>CO.CN(C=O)C.ClCCl.C(OCC)(=O)C.C(O)(=O)C.[OH-].[Pd+2].[OH-]>[F:40][C:21]1[CH:22]=[C:23]([NH:26][C:27](=[O:39])[C:28]([NH:30][CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:29])[CH:24]=[CH:25][C:20]=1[O:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:41][CH3:42])[CH:11]=2)[N:16]=[CH:15][CH:14]=1

Komponenten

8

Edukt 1

HCID 57810393N1-[3-Fluoro-4-[[6-methoxy-7-(phenylmethoxy)-4-quinolinyl]oxy]phenyl]-N2-(2-phenylethyl)ethanediamide

Produkt 1

HCID 136168658HCID 136168658, VerbindungAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 9942167Palladium hydroxideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-{4-[(7-benzyloxy-6-methoxyquinolin-4-yl)oxy]-3-fluorophenyl}-N′-(2-phenylethyl)ethanediamide (32 g, 56 mmol) in methanol (200 mL), DMF (100 mL), dichloromethane (100 mL), ethyl acetate (100 mL) and acetic acid (5 mL) was added palladium hydroxide (4.2 g) and the mixture was shaken on a Parr hydrogenator under a hydrogen pressure of 45 psi for 4 h. The resulting suspension was filtered through celite and the solid residue was washed with boiling dichloromethane (2 L) and acetone (2 L). The combined filtrates were evaporated to yield N-{3-fluoro-4-[(7-hydroxy-6-methoxyquinolin-4-yl)oxy]phenyl}-N′-(2-phenylethyl)ethanediamide as an off-white solid (25.6 g, 95%). 1H NMR (400 MHz, d6-DMSO): δ 11.06 (s, 1H), 10.25 (br s, 1H), 9.12 (t, 1H), 8.40 (d, 1H), 8.01 (dd, 1H), 7.50-7.44 (m, 2H), 7.31-7.23 (m, 6H), 6.39 (d, 1H), 3.95 (s, 3H), 2.85 (t, 2H), 2.50 (m, 2H); IR (cm−1): 1666, 1624, 1585, 1520, 1481, 1427, 1377, 1256, 1211, 1194, 1022, 880, 850, 839, 802, 750, 700; LC/MS (M+H=476).

Aufarbeitung

  1. filtrationThe resulting suspension was filtered through celite
  2. washthe solid residue was washed with boiling dichloromethane (2 L) and acetone (2 L)
  3. customThe combined filtrates were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1c2670de567a41b0a058979c7b161ec9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067436B2

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