2-Methylpyridine-5-boronic acid → HCID 118195100, compound

HRID 923951Notes

Reaction equation

HRID 923951 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:27][CH2:26][CH2:25][CH: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][CH: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 89907350HCID 89907350, compound

Product 1

HCID 118195100HCID 118195100, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 118 using 5-bromo-6-(3-hydroxypiperidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 118.1) and (6-methylpyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.88 min, m/z=473.1-474.1 [M+H]+, m/z=471.1-472.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.38 (m, 2H) 1.53-1.61 (m, 1H) 1.79-1.86 (m, 1H) 2.53 (s, 3H) 2.57 (dd, J=12.10, 9.17 Hz, 1H) 2.72 (t, J=10.51 Hz, 1H) 3.35-3.41 (m, 1H) 3.42-3.51 (m, 1H) 3.56-3.63 (m, 1H) 4.73 (d, J=4.40 Hz, 1H) 7.34-7.39 (m, 3H) 7.86 (d, J=8.80 Hz, 2H) 7.90 (dd, J=8.07, 2.20 Hz, 1H) 8.06 (d, J=2.20 Hz, 1H) 8.67 (d, J=1.96 Hz, 1H) 8.74 (d, J=2.20 Hz, 1H) 10.29 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-5bc1ac6af5dc461aa3c1431dd44da26a
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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