4-(Trifluoromethyl)piperidine → HCID 86281399, compound

HRID 2178484Notes

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]=[C:23]([F:28])[CH:24]=5)[N:19]=4)=[CH:15][C:10]=3[N:9]=[C:8]2[C@H:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]2[C:35]([OH:37])=[O:36])=[CH:4][CH:3]=1.[F:40][C:41]([F:49])([F:48])[CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>>[F:28][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([CH2:17][O:16][C:14]1[CH:13]=[CH:12][C:11]3[N:7]([CH2:6][C:5]4[CH:4]=[CH:3][C:2]([N:45]5[CH2:46][CH2:47][CH:42]([C:41]([F:49])([F:48])[F:40])[CH2:43][CH2:44]5)=[CH:39][CH:38]=4)[C:8]([C@H:29]4[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]4[C:35]([OH:37])=[O:36])=[N:9][C:10]=3[CH:15]=1)[CH:27]=[CH:26]2

Participants

Reactant 2

HCID 1364694-(Trifluoromethyl)piperidine

HCID 90414269HCID 90414269, compound

Product 1

HCID 86281399HCID 86281399, compound

Procedure

The title compound was prepared using analogous conditions to those described in Example 190 using racemic cis-2-(1-(4-bromobenzyl)-5-((6-fluoroquinolin-2-yl)methoxy)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid and 4-(trifluoromethyl)piperidine. MS (ESI): mass calcd. for C37H36F4N4O3, 660.27; m/z found, 661.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.40 (d, J=8.6, 1H), 8.15-8.08 (m, 1H), 7.78 (d, J=8.6, 1H), 7.69-7.60 (m, 2H), 7.57 (d, J=9.1, 1H), 7.37-7.28 (m, 2H), 7.13-7.02 (m, 4H), 5.68 (d, J=3.9, 2H), 5.49 (s, 2H), 3.82-3.76 (m, 2H), 3.65-3.57 (m, 1H), 2.92-2.88 (m, 1H), 2.88-2.80 (m, 2H), 2.43-2.25 (m, 2H), 2.22-2.15 (m, 1H), 2.05-1.93 (m, 4H), 1.82-1.63 (m, 4H), 1.57-1.47 (m, 2H).

Sources & evidence

ORD record: ord-6ce211a674bf4c96968932a259c3eeba
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067917B2

Reaction notes

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