4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole → 1-({5-(Quinolin-2-ylmethoxy)-1-[4-(1,3-thiazol-4-yl)benzyl]-1H-benzimidazol-2-yl}methyl)cyclopentanecarboxylic acid
Reaction equation
Br[C:2]1[CH:40]=[CH:39][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[CH2:28][C:29]2([C:34]([O:36]CC)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:4][CH:3]=1.[S:41]1[CH:45]=[C:44](B2OC(C)(C)C(C)(C)O2)[N:43]=[CH:42]1>>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[CH2:17][O:16][C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH2:6][C:5]3[CH:39]=[CH:40][C:2]([C:44]4[N:43]=[CH:42][S:41][CH:45]=4)=[CH:3][CH:4]=3)[C:8]([CH2:28][C:29]3([C:34]([OH:36])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]3)=[N:9][C:10]=2[CH:15]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared using similar methods to those in Example 97 using ethyl 1-((1-(4-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate and thiazole-4-boronic acid pinacol ester in Step A. MS (ESI): mass calcd. for C34H30N4O3S, 574.20; m/z found, 575.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.90-8.86 (m, 1H), 8.21 (d, J=8.5 Hz, 1H), 8.11 (d, J=8.4 Hz, 1H), 7.88 (d, J=8.3 Hz, 2H), 7.86-7.82 (m, 1H), 7.78-7.72 (m, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.59-7.54 (m, 1H), 7.54-7.51 (m, 1H), 7.40-7.35 (m, 1H), 7.22-7.17 (m, 1H), 7.13-7.05 (m, 3H), 5.43 (s, 2H), 5.38 (s, 2H), 3.14 (s, 2H), 2.38-2.28 (m, 2H), 1.76-1.67 (m, 2H), 1.58-1.49 (m, 4H).
Sources & evidence
- ORD record
- ord-34c4332fb05f4fd7ac150efe3cc1c92c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067917B2
Reaction notes
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