(Pyrimidin-5-yl)boronic acid → (R)-N-(3-Fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

HRID 924055Notes

Reaction equation

HRID 924055 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[C:12]([F:21])[CH:11]=1)=[O:8].[N:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=1>>[F:21][C:12]1[CH:11]=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:22]=[C:2]([C:33]3[CH:34]=[N:29][CH:30]=[N:31][CH:32]=3)[C:3]([N:23]3[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]3)=[N:4][CH:5]=2)[CH:15]=[CH:14][C:13]=1[O:16][C:17]([F:20])([F:19])[F:18]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86702607(R)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195362(R)-N-(3-Fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using (R)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 198.1) and pyrimidin-5-ylboronic acid to afford a white powder. HPLC (Condition 4) tR=4.88 min, UPLC-MS (Condition 3) tR=0.96 min, m/z=464.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.77 (m, 1H) 1.79-1.92 (m, 1H) 2.78-2.94 (m, 1H) 3.15-3.25 (m, 2H) 3.32-3.48 (m, 1H) 4.13-4.26 (m, 1H) 4.87 (d, J=3.52 Hz, 1H) 7.46-7.65 (m, 2H) 7.91-8.00 (m, 1H) 8.07 (d, J=2.35 Hz, 1H) 8.78 (d, J=2.35 Hz, 1H) 8.87 (s, 2H) 9.18 (s, 1H) 10.30 (s, 1H).

Workup

  1. customto afford a white powder

Sources & evidence

ORD record
ord-240c0b7b1fd34879ad619d48249bdfd6
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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