4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole → racemic cis-2,2-Dimethyl-3-{5-(quinolin-2-ylmethoxy)-1-[4-(1,3-thiazol-4-yl)benzyl]-1H-benzimidazol-2-yl}cyclopropanecarboxylic acid
Reaction equation
Br[C:2]1[CH:39]=[CH:38][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:28]2[C@H:30]([C:31]([O:33]CC)=[O:32])[C:29]2([CH3:37])[CH3:36])=[CH:4][CH:3]=1.[S:40]1[CH:44]=[C:43](B2OC(C)(C)C(C)(C)O2)[N:42]=[CH:41]1>>[CH3:36][C:29]1([CH3:37])[C@H:28]([C:8]2[N:7]([CH2:6][C:5]3[CH:38]=[CH:39][C:2]([C:43]4[N:42]=[CH:41][S:40][CH:44]=4)=[CH:3][CH:4]=3)[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:15][C:10]=3[N:9]=2)[C@@H:30]1[C:31]([OH:33])=[O:32]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared using similar methods to those in Example 97 using racemic cis-ethyl 3-(1-(4-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylcyclopropanecarboxylate and thiazole-4-boronic acid pinacol ester in Step A. MS (ESI): mass calcd. for C33H28N4O3S, 560.19; m/z found, 561.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.89-8.85 (m, 1H), 8.20 (d, J=8.5, 1H), 8.11 (d, J=8.5, 1H), 7.92 (d, J=8.3, 2H), 7.85-7.81 (m, 1H), 7.77-7.71 (m, 1H), 7.68 (d, J=8.5, 1H), 7.57-7.53 (m, 2H), 7.34-7.31 (m, 1H), 7.25-7.23 (m, 1H), 7.16-7.08 (m, 3H), 5.47-5.33 (m, 4H), 2.30 (d, J=8.2, 1H), 2.08 (d, J=8.2, 1H), 1.21 (s, 3H), 1.01 (s, 3H).
Sources & evidence
- ORD record
- ord-287bd8dcb51341d49b3e78ee614df877
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067917B2
Reaction notes
Loading…