(Pyrimidin-5-yl)boronic acid → HCID 118195371, compound

HRID 923995Notes

Reaction equation

HRID 923995 reaction equation
Br[C:2]1[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[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].[N:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[N:30][CH:29]=1>>[CH2:26]([N:22]([CH2:23][CH2:24][OH:25])[C:3]1[C:2]([C:32]2[CH:33]=[N:28][CH:29]=[N:30][CH:31]=2)=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])=[CH:5][N:4]=1)[CH3:27]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 899065775-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195371HCID 118195371, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using 5-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 156.1) and pyrimidin-5-ylboronic acid to afford a white solid. UPLC-MS (Condition 3) tR=0.97 min, m/z=448.3 [M+H]+, m/z=446.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.89 (t, J=6.96 Hz, 3H) 3.11-3.16 (m, 2H) 3.34-3.41 (m, 2H) 3.49 (q, J=5.65 Hz, 2H) 4.62 (t, J=5.27 Hz, 1H) 7.36 (d, J=8.41 Hz, 2H) 7.80-7.90 (m, 2H) 8.11 (d, J=2.38 Hz, 1H) 8.78 (d, J=2.26 Hz, 1H) 9.03 (s, 2H) 9.21 (s, 1H) 10.26 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-88c36bb0c4ab41ea843e3790492b1931
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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