(Pyrimidin-5-yl)boronic acid → 6-(3-(2-Hydroxypropan-2-yl)azetidin-1-yl)-5-(pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide
Reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([C:26]([OH:29])([CH3:28])[CH3:27])[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].[N:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1>>[OH:29][C:26]([CH:24]1[CH2:25][N:22]([C:3]2[C:2]([C:34]3[CH:35]=[N:30][CH:31]=[N:32][CH:33]=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)([CH3:28])[CH3:27]Participants
3
Procedure
The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-(2-hydroxypropan-2-yl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 142.1) and pyrimidin-5-ylboronic acid to afford an off-white powder. HPLC (Condition 4) tR=4.88 min, UPLC-MS (Condition 7) m/z=474.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.94 (s, 6H) 2.50-2.58 (m, 1H) 3.63 (d, J=7.43 Hz, 4H) 4.39 (s, 1H) 7.34 (d, J=8.99 Hz, 2H) 7.49-7.68 (m, 1H) 7.79-7.91 (m, 2H) 8.06 (dd, J=2.15, 0.98 Hz, 1H) 8.73-8.81 (m, 1H) 8.85-8.96 (m, 1H) 9.20 (d, J=0.78 Hz, 1H) 10.19 (s, 1H).
Workup
- customto afford an off-white powder
Sources & evidence
- ORD record
- ord-07081c946dc9458a92d91c086c78f8fa
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278981B2
Reaction notes
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