2-Methylpyridine-5-boronic acid → HCID 118195387, compound

HRID 923955Notes

Reaction equation

HRID 923955 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([OH:28])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:29][C:30]1[N:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[OH:28][C@@H:24]1[CH2:25][CH2:26][CH2:27][N:22]([C:3]2[C:2]([C:33]3[CH:34]=[N:35][C:30]([CH3:29])=[CH:31][CH:32]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 89907836HCID 89907836, compound

Product 1

HCID 118195387HCID 118195387, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 118 using (R)-5-bromo-6-(3-hydroxypiperidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 121.1) and (6-methylpyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=2.28 min, m/z=473.1 [M+H]+, m/z=471.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.18-1.39 (m, 2H) 1.53-1.62 (m, 1H) 1.77-1.86 (m, 1H) 2.54 (s, 3H) 2.55-2.62 (m, 1H) 2.68-2.77 (m, 1H) 3.42-3.51 (m, 2H) 3.55-3.63 (m, 1H) 4.72 (s, 1H) 7.36 (d, J=9.05 Hz, 2H) 7.40 (d, J=8.07 Hz, 1H) 7.83-7.88 (m, 2H) 7.92-7.98 (m, 1H) 8.07 (d, J=1.96 Hz, 1H) 8.67-8.72 (m, 1H) 8.75 (d, J=2.20 Hz, 1H) 10.29 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-a811adbcd30b441592dc6502f7e8a5a6
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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