3,3-Difluoroazetidine → HCID 86270472, compound

HRID 1848727Notes

Reaction equation

HRID 1848727 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.[F:35][C:36]1([F:40])[CH2:39][NH:38][CH2:37]1>>[F:35][C:36]1([F:40])[CH2:39][N:38]([C:2]2[CH:34]=[CH:33][C:5]([CH2:6][N:7]3[C:11]4[CH:12]=[C:13]([O:16][CH2:17][C:18]5[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=5)[CH:14]=[CH:15][C:10]=4[N:9]=[C:8]3[C@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]3[C:30]([OH:32])=[O:31])=[CH:4][CH:3]=2)[CH2:37]1

Participants

3

Reactant 2

HCID 27582483,3-DifluoroazetidineHCID 90410111HCID 90410111, compound

Product 1

HCID 86270472HCID 86270472, 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 3,3-difluoroazetidine. MS (ESI): mass calcd. for C29H31F2N5O3, 535.24; m/z found, 536.3 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 7.52 (d, J=9.6, 2H), 7.04 (d, J=8.2, 2H), 6.96 (s, 1H), 6.91 (d, J=8.8, 1H), 6.52 (d, J=8.3, 2H), 6.26 (s, 1H), 5.44 (d, J=16.5, 1H), 5.38 (d, J=16.4, 1H), 4.99 (s, 2H), 4.17 (t, J=11.9, 4H), 3.83 (s, 3H), 3.59-3.53 (m, 1H), 2.88-2.78 (m, 1H), 2.41-2.29 (m, 1H), 1.98 (s, 1H), 1.79 (t, J=27.9, 5H), 1.53-1.38 (m, 1H).

Sources & evidence

ORD record
ord-55935d8139e344f388cac4d213ad0af0
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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