2-Methylpyridine-5-boronic acid → 4-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-(6-methylpyridin-3-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:26][C@H:25]([OH:27])[C@@H:24]([OH:28])[CH2:23]1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[CH3:29][C:30]1[N:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[OH:28][C@@H:24]1[C@@H:25]([OH:27])[CH2:26][N:22]([C:21]2[CH:20]=[CH:19][C:4]([C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=3)=[O:6])=[CH:3][C:2]=2[C:33]2[CH:34]=[N:35][C:30]([CH3:29])=[CH:31][CH:32]=2)[CH2:23]1Participants
3
Procedure
The title compound was prepared in an analogous fashion to that described in Example 7 using 3-bromo-4-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 7.1) and (6-methylpyridin-3-yl)boronic acid to afford a yellow solid. UPLC-MS (condition 1) tR=1.65 min, m/z=474.0 [M+H]+, m/z=472.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.53 (s, 3H) 2.74 (d, J=10.76 Hz, 2H) 3.25 (dd, J=10.51, 3.67 Hz, 2H) 3.85 (br. s, 2H) 5.03 (br. s, 2H) 6.90 (d, J=8.80 Hz, 1H) 7.27-7.38 (m, 3H) 7.68 (dd, J=7.82, 2.20 Hz, 1H) 7.77 (d, J=2.20 Hz, 1H) 7.85-7.88 (m, 2H) 7.87-7.91 (m, 1H) 8.48 (d, J=2.20 Hz, 1H) 10.09 (s, 1H).
Workup
- customto afford a yellow solid
Sources & evidence
- ORD record
- ord-a2376eb9714940c89d338fe3e53b55a3
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278981B2
Reaction notes
Loading…