(Pyrimidin-5-yl)boronic acid → N-(4-(Chlorodifluoromethoxy)phenyl)-6-(cis-3,4-dihydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide
Reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][C@H:25]([OH:27])[C@H:24]([OH:28])[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]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=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:33]3[CH:34]=[N:29][CH:30]=[N:31][CH:32]=3)[C:3]([N:22]3[CH2:26][C@H:25]([OH:27])[C@H:24]([OH:28])[CH2:23]3)=[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 244 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(cis-3,4-dihydroxypyrrolidin-1-yl)nicotinamide (Stage 249.1) and pyrimidin-5-ylboronic acid to afford a white solid. UPLC-MS (Condition 3) tR=0.87 min, m/z=478.1 [M+H]+, m/z=476.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 3.05 (dd, J=11.00, 4.40 Hz, 2H) 3.26 (dd, J=10.64, 5.26 Hz, 2H) 3.94-4.02 (m, 2H) 4.88 (d, J=4.65 Hz, 2H) 7.34 (d, J=9.05 Hz, 2H) 7.81-7.90 (m, 2H) 8.10 (d, J=2.20 Hz, 1H) 8.79 (d, J=2.20 Hz, 1H) 8.88 (s, 2H) 9.20 (s, 1H) 10.18 (s, 1H).
Workup
- customto afford a white solid
Sources & evidence
- ORD record
- ord-faaa5318c0e74f1a9994c9ea832a5e5c
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278981B2
Reaction notes
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