Reaction equation
Br[C:2]1[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[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:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=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:31]3[CH:32]=[N:27][CH:28]=[N:29][CH:30]=3)[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=2)=[CH:11][CH:12]=1Participants
3
Procedure
The title compound was prepared in an analogous fashion to that described in Example 169 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((2-hydroxyethyl)(methyl)amino)nicotinamide (Stage 179.1) and pyrimidin-5-ylboronic acid to afford a white crystalline solid. HPLC (Condition 4) tR=5.02 min, UPLC-MS (Condition 3) tR=0.96 min, m/z=450.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.69 (s, 3H) 3.38-3.65 (m, 4H) 4.67 (t, J=5.08 Hz, 1H) 7.34 (d, J=8.21 Hz, 2H) 7.85 (d, J=8.99 Hz, 2H) 8.13 (d, J=2.35 Hz, 1H) 8.75 (d, J=1.56 Hz, 1H) 8.95 (s, 2H) 9.17 (s, 1H) 10.22 (s, 1H).
Workup
- customto afford a white crystalline solid
Sources & evidence
- ORD record
- ord-82ae520a3094460793d915d3fde4ac35
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278981B2
Linked notes
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