6-Bromo-1-methylquinolin-2(1H)-one → 3-(2-Methyl-4-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yl)but-3-yn-2-yl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1422648Notes

Reaction equation

HRID 1422648 reaction equation
O[C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:15][C:16]([CH3:18])=[CH2:17])[CH2:3][CH2:4][N:5]([C:10]([CH3:14])([C:12]#[CH:13])[CH3:11])[C:6](=[O:9])[O:7]C.Br[C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH3:36])[C:31](=[O:37])[CH:30]=[CH:29]2>>[CH3:14][C:10]([N:5]1[CH2:4][CH2:3][C:2]([CH2:15][C:16]([CH3:18])=[CH2:17])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:7][C:6]1=[O:9])([C:12]#[C:13][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH3:36])[C:31](=[O:37])[CH:30]=[CH:29]2)[CH3:11]

Participants

3

Reactant 2

HCID 218161626-Bromo-1-methylquinolin-2(1H)-oneHCID 86669141Methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-methylbut-3-yn-2-yl)carbamate

Product 1

HCID 509057363-(2-Methyl-4-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yl)but-3-yn-2-yl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

Procedure

The title compound was prepared from methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-methylbut-3-yn-2-yl)carbamate and 6-bromo-1-methylquinolin-2(1H)-one following procedures analogous to those described in Example 1 Steps 3 and 4. LC-MS Method 1 tR=1.92 min, m/z=455; 1H NMR (CDCl3) 1.64 (s, 3H), 1.69 (s, 3H), 1.82 (s, 6H), 2.26 (m, 1H), 2.40 (m, 1H), 2.61 (AB quartet, 2H), 3.08 (m, 1H), 3.64 (m, 1H), 3.71 (s, 3H), 4.64 (s, 1H), 4.83 (s, 1H), 6.77 (d, 1H), 7.25-7.65 (9H).

Sources & evidence

ORD record
ord-2a23f0d305ec442d84f7d67968bd71ec
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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