6-bromo-4-(4-methoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one → rac-(4aR*,8aR*)-3-(4-(4-methoxybenzyl)-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)octahydro-2H-pyrido[4,3-e][1,3]oxazin-2-one

HRID 571974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571974
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:21])[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:10]=2[N:11]=1.[O:22]=[C:23]1[NH:28][CH2:27][CH:26]2[CH2:29][CH2:30][N:31](C(OC(C)(C)C)=O)[CH2:32][CH:25]2[O:24]1>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:9]2[C:8](=[O:21])[CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([N:28]4[CH2:27][CH:26]5[CH2:29][CH2:30][NH:31][CH2:32][CH:25]5[O:24][C:23]4=[O:22])=[N:11][C:10]2=3)=[CH:14][CH:15]=1

Komponenten

3

Edukt 2

HCID 866493756-bromo-4-(4-methoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-oneHCID 89602371rac-(4aR*,8aR*)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate

Produkt 1

HCID 117641657rac-(4aR*,8aR*)-3-(4-(4-methoxybenzyl)-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)octahydro-2H-pyrido[4,3-e][1,3]oxazin-2-oneAusbeute 95 %

Versuchsvorschrift

Starting from 6-bromo-4-(4-methoxybenzyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (prepared as described in WO 2010/041194, 0.35 g, 1 mmol) and rac-(4aR*,8aR*)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate (Preparation A, 0.308 g, 1.2 mmol, 1.2 eq.), the title compound was obtained as an orange foam (0.255 g) using the procedures described in Preparation D, steps D.i and D.ii (Buchwald coupling: 95% yield, Boc deprotection: 63% yield).

Quellen und Nachweise

ORD-Eintrag
ord-2f92d0741b944fe2a112eabad460a8d2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029368B2

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