2-Methylpyridine-5-boronic acid → HCID 118195279, compound

HRID 923859Notes

Reaction equation

HRID 923859 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[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].[CH3:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:32]3[CH:33]=[N:34][C:29]([CH3:28])=[CH:30][CH:31]=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 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195279HCID 118195279, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 36 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and (6-methylpyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.60 min, m/z=459.0 [M+H]+, m/z=457.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.73 (dd, J=8.07, 3.91 Hz, 1H) 1.77-1.89 (m, 1H) 2.55 (s, 3H) 2.88 (d, J=11.74 Hz, 1H) 3.17-3.27 (m, 2H) 3.42 (br. s, 1H) 4.19 (br. s, 1H) 4.84 (br. s, 1H) 7.34 (d, J=8.31 Hz, 2H) 7.39 (d, J=7.83 Hz, 1H) 7.75 (dd, J=7.95, 1.83 Hz, 1H) 7.85 (d, 2H) 8.00 (d, J=2.45 Hz, 1H) 8.52 (d, J=1.96 Hz, 1H) 8.75 (d, J=2.20 Hz, 1H) 10.16 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-34d985cbcb714312bde962593a29a941
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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