2-Methylpyridine-4-boronic acid → N-methyl-N-(2-((S)-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)ethyl)methanesulfonamide

HRID 1046178Notes

Reaction equation

HRID 1046178 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][CH2:23][N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:30])[CH3:9])=[CH:4][CH:3]=1.[CH3:31][C:32]1[CH:37]=[C:36](B(O)O)[CH:35]=[CH:34][N:33]=1>>[CH3:29][N:24]([CH2:23][CH2:22][C@@:13]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:12][C:11](=[O:30])[N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:36]3[CH:35]=[CH:34][N:33]=[C:32]([CH3:31])[CH:37]=3)=[CH:3][CH:4]=2)[CH3:9])[CH2:15][CH2:14]1)[S:25]([CH3:28])(=[O:27])=[O:26]

Participants

3

Reactant 2

HCID 41926642-Methylpyridine-4-boronic acidHCID 58109217HCID 58109217, compound

Product 1

HCID 58109460N-methyl-N-(2-((S)-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)ethyl)methanesulfonamide

Procedure

The title compound was prepared from N-(2-((S)-3-((S)-1-(4-bromophenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)ethyl)-N-methylmethanesulfonamide and 2-methylpyridine-4-boronic acid following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=0.989, m/z=508.1; 1H NMR (CDCl3) 1.53 (d, 3H), 2.17-2.32 (m, 5H), 2.63 (s, 3H), 2.71 (s, 3H), 2.81 (s, 3H), 2.93 (m, 2H), 3.22 (m, 1H), 5.67 (m, 1H), 7.08 (m, 2H), 7.21 (s, 2H), 7.25 (m, 3H), 7.33 (m, 2H), 7.61 (s, 1H), 7.71 (d, 1H), 8.72 (d, 1H).

Sources & evidence

ORD record
ord-38ee5a43ddd742559ac810e0d219d746
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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