4-Fluoropiperidine → HCID 86270283, compound

HRID 1848725Notes

Reaction equation

HRID 1848725 reaction equation
Br[C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][C:18]4[C:22]([Cl:23])=[CH:21][N:20]([CH3:24])[N:19]=4)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@H:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]2[C:31]([OH:33])=[O:32])=[CH:4][CH:3]=1.[F:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>>[Cl:23][C:22]1[C:18]([CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:10]3[N:9]=[C:8]([C@H:25]4[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]4[C:31]([OH:33])=[O:32])[N:7]([CH2:6][C:5]4[CH:34]=[CH:35][C:2]([N:40]5[CH2:41][CH2:42][CH:37]([F:36])[CH2:38][CH2:39]5)=[CH:3][CH:4]=4)[C:11]=3[CH:12]=2)=[N:19][N:20]([CH3:24])[CH:21]=1

Participants

3

Reactant 2

HCID 27591594-FluoropiperidineHCID 86269905HCID 86269905, compound

Product 1

HCID 86270283HCID 86270283, compound

Procedure

The title compound was prepared from racemic cis-2-(1-(4-bromobenzyl)-6-((4-chloro-1-methyl-1H-pyrazol-3-yl)methoxy)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid using analogous conditions described in Example 152 using 4-fluoropiperidine. MS (ESI): mass calcd. for C31H35ClFN5O3, 580.11; m/z found, 581.0 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 7.68 (t, J=4.5, 2H), 7.31 (d, J=2.1, 1H), 7.26 (dd, J=9.0, 2.3, 1H), 7.14-7.02 (m, 4H), 5.70 (s, 2H), 5.03 (s, 2H), 4.79-4.68 (m, 1H), 3.81 (s, 3H), 3.66-3.53 (m, 1H), 3.51-3.36 (m, 2H), 3.28-3.17 (m, 2H), 2.88 (s, 1H), 2.40-2.13 (m, 2H), 2.12-1.84 (m, 6H), 1.84-1.63 (m, 2H), 1.61-1.46 (m, 2H).

Sources & evidence

ORD record
ord-f42b0bda676d4660acf76587a65949b0
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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