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 571974Notes

Reaction equation

HRID 571974 reaction equation
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

Participants

3

Reactant 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

Product 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-oneYield 95%

Procedure

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).

Sources & evidence

ORD record
ord-2f92d0741b944fe2a112eabad460a8d2
Source dataset
uspto-grants-2015_05
Patent number
US09029368B2

Reaction notes

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