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

HRID 470424Notes

Reaction equation

HRID 470424 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.[O:30]=[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][NH: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:34]4[CH:35]=[CH:36][C:31](=[O:30])[NH:32][CH:33]=4)=[CH:3][CH:4]=3)[CH3:9])[CH2:15][CH2:14]2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 467387646-Hydroxypyridine-3-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 596357573-((R)-6-(4-fluorophenyl)-2-oxo-3-((S)-1-(4-(6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-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-oxo-1,2-dihydropyridin-5-ylboronic acid following a procedure analogous to that described in Example 4. LC-MS Method 1 tR=1.37 min, m/z=474(M+1); 1H NMR (CDCl3) 7.97, (dd, 1H), 7.73(s, 1H), 7.33(m, 2H), 7.20(d, 2H), 7.17(t, 2H), 6.98(m, 3H), 5.67(q, 1H), 3.00(dt, 1H), 2.49(m, 2H), 2.30(m, 1H), 2.13(s, 2H), 1.55(d, 3H), 1.45(s, 3H), 1.34(s, 3H).

Sources & evidence

ORD record
ord-817dea67a1a3432fba1ed29024c4ef76
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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