5-Bromo-1-methylpyridin-2(1H)-one → (6S)-6-(2-Hydroxyethyl)-3-[(1S)-1-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]propyl]-6-phenyl-1,3-oxazinan-2-one

HRID 406684Notes

Reaction equation

HRID 406684 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:11]2[CH2:16][CH2:15][C@:14]([CH2:23][CH2:24][OH:25])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:13][C:12]2=[O:26])[CH2:9][CH3:10])=[CH:4][CH:3]=1.Br[C:28]1[CH:29]=[CH:30][C:31](=[O:35])[N:32]([CH3:34])[CH:33]=1>>[OH:25][CH2:24][CH2:23][C@@:14]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:13][C:12](=[O:26])[N:11]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:28]3[CH:29]=[CH:30][C:31](=[O:35])[N:32]([CH3:34])[CH:33]=3)=[CH:3][CH:4]=2)[CH2:9][CH3:10])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 130240275-Bromo-1-methylpyridin-2(1H)-oneHCID 66600735HCID 66600735, compound

Product 1

HCID 59635712(6S)-6-(2-Hydroxyethyl)-3-[(1S)-1-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]propyl]-6-phenyl-1,3-oxazinan-2-one

Procedure

The title compound was prepared from (S)-3-((S)-1-(4-bromophenyl)propyl)-6-(2-hydroxyethyl)-6-phenyl-1,3-oxazinan-2-one following a procedure analogous to that described in Example 18 using 5-bromo-1-methylpyridin-2(1H)-one in Step 2. LC-MS Method 2 tR=1.627 min, m/z=447.1; 1H NMR (CDCl3) 1.06 (m, 3H), 1.87-2.06 (m, 2H), 2.11-2.28 (m, 2H), 2.33 (m, 3H), 2.96 (m, 1H), 3.53 (m, 1H), 3.62 (s, 3H), 3.78 (m, 1H), 5.48 (m, 1H), 6.69 (m, 1H),7.03 (m, 2H), 7.14 (m, 2H), 7.21-7.38 (m, 4H), 7.41 (s, 1H), 7.56 (m, 1H).

Sources & evidence

ORD record
ord-45ff6ed34b8343adb82980b5199306dc
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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