Piperidine → HCID 86270284, compound

HRID 1848726Notes

Reaction equation

HRID 1848726 reaction equation
Br[C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][C:18]4[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=4)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]2[C:30]([OH:32])=[O:31])=[CH:4][CH:3]=1.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH3:23][N:20]1[CH:21]=[CH:22][C:18]([CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:10]3[N:9]=[C:8]([C@H:24]4[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]4[C:30]([OH:32])=[O:31])[N:7]([CH2:6][C:5]4[CH:4]=[CH:3][C:2]([N:35]5[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]5)=[CH:34][CH:33]=4)[C:11]=3[CH:12]=2)=[N:19]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 90410111HCID 90410111, compound

Product 1

HCID 86270284HCID 86270284, compound

Procedure

The title compound was prepared from racemic cis-2-(1-(4-bromobenzyl)-6-((1-methyl-1H-pyrazol-3-yl)methoxy)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid using analogous conditions to Example 152 using piperidine. MS (ESI): mass calcd. for C31H37N5O3, 527.67; m/z found, 528.3 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 7.51 (dd, J=8.2, 5.5, 2H), 7.01 (d, J=8.7, 2H), 6.97 (d, J=2.3, 1H), 6.94-6.87 (m, 3H), 6.27 (d, J=2.3, 1H), 5.45-5.34 (m, 2H), 4.99 (s, 2H), 3.83 (s, 3H), 3.63-3.53 (m, 1H), 3.15-3.06 (m, 4H), 2.85-2.76 (m, 1H), 2.43-2.25 (m, 1H), 1.99-1.75 (m, 4H), 1.74-1.63 (m, 5H), 1.63-1.52 (m, 2H), 1.53-1.34 (m, 2H).

Sources & evidence

ORD record
ord-e4a82141b5da4f6e93f479a133034834
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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