(3-Chloro-4-(dimethylcarbamoyl)phenyl)boronic acid → 2-Chloro-4-(5-((1R,2R)-1-(3-fluorophenyl)-2-methyl-3-oxo-3-(1,3,4-thiadiazol-2-ylamino)propyl)-2-thienyl)-N,N-dimethylbenzamide
Reaction equation
Br[C:2]1[S:6][C:5]([C@@H:7]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[C@@H:8]([CH3:17])[C:9]([NH:11][C:12]2[S:13][CH:14]=[N:15][N:16]=2)=[O:10])=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[C:32](=[O:36])[N:33]([CH3:35])[CH3:34]>>[Cl:25][C:26]1[CH:27]=[C:28]([C:2]2[S:6][C:5]([C@@H:7]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[C@@H:8]([CH3:17])[C:9](=[O:10])[NH:11][C:12]3[S:13][CH:14]=[N:15][N:16]=3)=[CH:4][CH:3]=2)[CH:29]=[CH:30][C:31]=1[C:32]([N:33]([CH3:35])[CH3:34])=[O:36]Participants
Reactant 2
Product 1
Procedure
In a similar manner to Example 43, the Suzuki coupling reaction of the title compound of Example 97, (2R,3R)-3-(5-bromothiophen-2-yl)-3-(3-fluorophenyl)-2-methyl-N-(1,3,4-thiadiazol-2-yl)propanamide (240 mg, 0.563 mmol), and 3-chloro-4-(dimethyl-carbamoyl)phenylboronic acid (256 mg, 1.126 mmol) afforded the title compound of Example 110 (147 mg, 0.278 mmol, 49.4% yield). 1H NMR (400 MHz, MeOD) δ ppm 8.96 (1H, s) 7.71 (1H, d, J=1.51 Hz) 7.61 (1H, dd, J=7.93, 1.64 Hz) 7.39 (1H, d, J=3.78 Hz) 7.33 (1H, d, J=8.06 Hz) 7.19-7.28 (2H, m) 7.15 (1H, dd, J=10.07, 2.01 Hz) 7.11 (1H, d, J=3.78 Hz) 6.83-6.89 (1H, m) 4.51 (1H, d, J=1.33 Hz) 3.48-3.57 (1H, m) 3.11 (3H, s) 2.91 (3H, s) 1.32 (3H, d, J=6.55 Hz). LC/MS (m/z) 529.11 (M+H)+]; HPLC Rt: 3.448 min.
Sources & evidence
- ORD record
- ord-6c0f094d4f8d434497b2ce321559e292
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222247B2
Reaction notes
Loading…