(Pyrimidin-5-yl)boronic acid → N-(4-(Chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)-5-(pyrimidin-5-yl)nicotinamide

HRID 924032Notes

Reaction equation

HRID 924032 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]([Cl: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>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:21]=[C:2]([C:32]3[CH:33]=[N:28][CH:29]=[N:30][CH:31]=3)[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[N:4][CH:5]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 899068415-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide

Product 1

HCID 89908393N-(4-(Chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)-5-(pyrimidin-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 169 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide (Stage 182.1) and pyrimidin-5-ylboronic acid to afford a light yellow foam. HPLC (Condition 4) tR=5.23 min, UPLC-MS (Condition 3) tR=1.01 min, m/z=464.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.87 (t, J=6.84 Hz, 3H) 3.14 (m, J=7.00 Hz, 2H) 3.32-3.54 (m, 4H) 4.61 (t, J=5.28 Hz, 1H) 7.34 (d, J=8.21 Hz, 2H) 7.84 (d, J=1.00 Hz, 2H) 8.10 (dd, J=2.35, 1.17 Hz, 1H) 8.77 (dd, J=2.35, 1.17 Hz, 1H) 9.01 (d, J=0.78 Hz, 2H) 9.19 (d, J=1.17 Hz, 1H) 10.26 (s, 1H).

Workup

  1. customto afford a light yellow foam

Sources & evidence

ORD record
ord-138e4d19effd4c76b5fddaf396e20046
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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