2-Methylpyridine-4-boronic acid → 3-((R)-6-(4-fluorophenyl)-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-2-oxo-1,3-oxazinan-6-yl)-2,2-dimethylpropanenitrile

HRID 2037702Notes

Reaction equation

HRID 2037702 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:23][C:24]([CH3:28])([CH3:27])[C:25]#[N:26])([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[O:12][C:11]2=[O:29])[CH3:9])=[CH:4][CH:3]=1.[CH3:30][C:31]1[CH:36]=[C:35](B(O)O)[CH:34]=[CH:33][N:32]=1>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C@:13]2([CH2:23][C:24]([CH3:28])([CH3:27])[C:25]#[N:26])[O:12][C:11](=[O:29])[N:10]([C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([C:35]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:30])[CH:36]=4)=[CH:3][CH:4]=3)[CH3:9])[CH2:15][CH2:14]2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 41926642-Methylpyridine-4-boronic acidHCID 596356553-((R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)-2,2-dimethylpropanenitrile

Product 1

HCID 581091903-((R)-6-(4-fluorophenyl)-3-((S)-1-(4-(2-methylpyridin-4-yl)phenyl)ethyl)-2-oxo-1,3-oxazinan-6-yl)-2,2-dimethylpropanenitrile

Procedure

The title compound was prepared from 3-((R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)-2,2-dimethylpropanenitrile and 2-methylpyridine-4-boronic acid following a procedure analogous to that described in Example 459 Step 1. LC-MS Method 2 tR=0.926, m/z=472.2; 1H NMR (CD3OD) 1.31 (s, 3H), 1.41 (s, 1H), 1.58 (d, 3H), 2.30 (m, 2H), 2.34 (m, 1H), 2.43 (m, 1H), 2.61 (d, 2H), 2.81 (s, 3H), 3.21 (m, 1H), 5.62 (m, 1H), 7.08 (m, 2H), 7.29 (d, 2H), 7.41 (m, 2H), 7.79 (d, 2H), 8.09 (m, 1H), 8.19 (s, 1H), 8.68 (d, 1H).

Sources & evidence

ORD record
ord-b21a3bd0468d4b2495f62ec5e7cfe084
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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