1-Hydroxybenzotriazole → N-(4-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 15516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15516
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=O)[C:9]2=[O:17])=[CH:4][CH:3]=1.[CH:18]1[CH:19]=[CH:20][C:21]2N(O)N=N[C:22]=2[CH:23]=1.CCN=C=NCCCN(C)C.Cl.[CH3:40][O:41][C:42]1[CH:43]=[C:44]2[C:49](=[CH:50][C:51]=1[O:52][CH3:53])[N:48]=[CH:47][CH:46]=[C:45]2[O:54][C:55]1[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][C:56]=1[F:62]>CN(C=O)C>[CH2:53]([O:52][C:51]1[CH:50]=[C:49]2[C:44]([C:45]([O:54][C:55]3[CH:60]=[CH:59][C:58]([NH:61][C:14]([C:10]4[C:9](=[O:17])[N:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)[CH:13]=[CH:12][CH:11]=4)=[O:16])=[CH:57][C:56]=3[F:62])=[CH:46][CH:47]=[N:48]2)=[CH:43][C:42]=1[O:41][CH3:40])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Produkt 1

HCID 58833040N-(4-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamideAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a mixture of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (74 mg, 0.32 mmol), HOBt (16 mg) and EDCI.HCl (65 mg, 0.34 mmol) in DMF (3 mL) was added a solution of 4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorobenzenamine (120 mg, 0.31 mmol) in DMF (3 mL) at rt, and the reaction mixture was stirred overnight at rt. It was directly purified by preparative HPLC to afford the product (46 mg, 20%) as a white TFA salt solid. 1H NMR (DMF-d7) δ 12.22 (s, 1H), 8.71 (d, 1H, J=6.0 Hz), 8.59 (d, 1H, J=7.2 Hz), 8.14-7.31 (m, 15H), 6.84 (d, 1H, J=5.5 Hz), 6.72 (t, 1H, J=7.2 Hz), 5.35 (s, 2H), 4.02 (s, 3H); MS(ESI+) m/z 606.3 (M+H)+.

Aufarbeitung

  1. customIt was directly purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-21800dd0b62449349295126bfd11879b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732613B2

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