(2-Methoxypyridin-4-yl)boronic acid → HCID 58109624, compound

HRID 1046207Notes

Reaction equation

HRID 1046207 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][CH2:17][CH2:18][OH:19])[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[CH:32][N:31]=1>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C@:13]2([CH2:16][CH2:17][CH2:18][OH:19])[O:12][C:11](=[O:27])[N:10]([C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([C:34]4[CH:33]=[CH:32][N:31]=[C:30]([O:29][CH3:28])[CH:35]=4)=[CH:3][CH:4]=3)[CH3:9])[CH2:15][CH2:14]2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 59532370(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxy-propyl)-1,3-oxazinan-2-one

Product 1

HCID 58109624HCID 58109624, compound

Procedure

The title compound was prepared from (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one and 2-methoxypyridin-4-ylboronic acid following a procedure analogous to that described in Example 14. LC-MS Method 1 tR=1.9 min, m/z=447 (M+1); 1H NMR (CDCl3) 8.29 (1H, d, J=5.5 Hz), 7.34 (2H, m), 7.21-7.15 (m, 3H), 7.02-6.93 (5H, m), 5.67-5.61 (1H, m), 4.05 (3H, s), 3.53 (1H, t, J=6.41 Hz), 2.97-2.93 (1H, m), 2.33-2.11 (3H, m), 2.06-1.83 (3H, m), 1.67-1.57 (1H, m), 1.50 (3H, d, J=7.03), 1.36-1.26 (1H, m).

Sources & evidence

ORD record
ord-8c737ada1e5342c386f72f20f27d4953
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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