Pyridine-2-boronic acid → HCID 58109283, compound

HRID 2037661Notes

Reaction equation

HRID 2037661 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][C:24]([NH2:26])=[O:25])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O>>[O:27]=[C:11]1[N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)=[CH:3][CH:4]=2)[CH3:9])[CH2:15][CH2:14][C@:13]([CH2:22][CH2:23][C:24]([NH2:26])=[O:25])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:12]1

Participants

3

Reactant 2

HCID 2762745Pyridine-2-boronic acidHCID 59635801HCID 59635801, compound

Product 1

HCID 58109283HCID 58109283, compound

Procedure

The title compound was prepared from 3-((R)-3-((S)-1-(4-bromophenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propanamide and pyridine-2-boronic acid following procedures analogous to those described in Example 75 Step 1. LC-MS Method 2 tR=0.932 min, m/z=430.1; 1H NMR (CDCl3) 1.52 (d, 3H), 1.90 (m, 1H), 2.13 (m, 1H), 2.21 (m, 4H), 2.45 (m, 1H), 2.82 (m, 1H), 5.15 (s, 1H), 5.35 (s, 1H), 5.65 (m, 1H), 6.98 (d, 2H), 7.13-7.32 (m, 6H), 7.56 (m, 1H), 7.65 (m, 3H), 8.57 (d, 1H).

Sources & evidence

ORD record
ord-9eaa2ba9db38451c845f655dc3c9e685
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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