Benzylethanolamine → 2-(2,6-Difluorophenyl)-5-(4-(2-(2-hydroxyethylamino)ethoxy)phenyl)oxazole-4-carboxamide

HRID 389774

Reaktionsgleichung

Reaktionsgleichung von HRID 389774
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]3[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=3[F:23])=[N:13][C:12]=2[C:24]([NH2:26])=[O:25])=[CH:7][CH:6]=1.C([NH:34][CH2:35][CH2:36][OH:37])C1C=CC=CC=1>CO.[Pd]>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:16]=1[C:14]1[O:15][C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:34][CH2:35][CH2:36][OH:37])=[CH:6][CH:7]=2)=[C:12]([C:24]([NH2:26])=[O:25])[N:13]=1

Komponenten

5

Edukt 2

HCID 4348BenzylethanolamineHCID 595873755-(4-(2-Chloroethoxy)phenyl)-2-(2,6-difluorophenyl)oxazole-4-carboxamide

Produkt 1

HCID 595874492-(2,6-Difluorophenyl)-5-(4-(2-(2-hydroxyethylamino)ethoxy)phenyl)oxazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound was prepared by reaction of 5-(4-(2-chloroethoxy)phenyl)-2-(2,6-difluorophenyl)oxazole-4-carboxamide with 2-(benzylamino)ethanol, according to the procedure described in example S-1, step c, followed by deprotection with the H-cube hydrogenation system (full H2 mode, 10% Pd\C catalyst, 1 ml/min, 60° C., 0.05M in MeOH). 1H NMR (DMSO) δ 2.79 (2H, t), 3.17 (2H, t), 3.55 (2H, t), 4.20 (2H, t), 7.05-7.15 (2H, m), 7.35-7.45 (2H, m), 7.60-7.80 (3H, m), 8.20-8.30 (2H, m). LCMS (2) 2.17 min; m/z (ES+) 404.

Quellen und Nachweise

ORD-Eintrag
ord-0f9fca43d48946b59259820417002df8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378095B2

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