3,3-Difluoroazetidine hydrochloride → HCID 90410157, compound

HRID 1848756Notes

Reaction equation

HRID 1848756 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[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][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])=[C:4]([F:36])[CH:3]=1.Cl.[F:38][C:39]1([F:43])[CH2:42][NH:41][CH2:40]1>>[F:38][C:39]1([F:43])[CH2:42][N:41]([C:2]2[CH:35]=[CH:34][C:5]([CH2:6][N:7]3[C:11]4[CH:12]=[C:13]([O:16][CH2:17][C:18]5[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=5)[CH:14]=[CH:15][C:10]=4[N:9]=[C:8]3[C@H:25]3[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]3[C:31]([OH:33])=[O:32])=[C:4]([F:36])[CH:3]=2)[CH2:40]1

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 86268480HCID 86268480, compound

Product 1

HCID 90410157HCID 90410157, compound

Procedure

The title compound was prepared in a manner analogous to that in Example 152 substituting (1S,2R)-2-{1-(4-bromo-2-fluorobenzyl)-6-[(5-methylpyridin-2-yl)methoxy]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acid and 3,3-difluoroazetidine hydrochloride. MS (ESI): mass calcd. for C31H31F3N4O3, 564.23; m/z found, 565.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.34 (5, 1H), 7.67-7.63 (m, 1H), 7.55 (d, J=8.6, 1H), 7.45 (d, J=8.0, 1H), 7.02-6.98 (m, 2H), 6.81 (t, J=8.5, 1H), 6.39 (dd, J=12.3, 2.3, 1H), 6.24 (dd, J=8.4, 2.3, 1H), 5.47 (d, J=16.6, 1H), 5.41 (d, J=16.6, 1H), 5.12 (5, 2H), 4.21 (t, J=12.0, 4H), 3.68-3.54 (m, 1H), 2.91-2.82 (m, 1H), 2.35 (s, 3H), 2.34-2.26 (m, 1H), 2.12-2.02 (m, 1H), 1.90-1.75 (m, 4H), 1.56-1.49 (m, 1H), 1.49-1.42 (m, 1H).

Sources & evidence

ORD record
ord-d66727919399492cbb7128a6dcf53854
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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