HCID 58548616, compound → HCID 178420806, compound

HRID 1846777Notes

Reaction equation

[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][CH:14]3[CH2:19][CH2:18][CH:17]([C:20]4[NH:24][C:23]5[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=5[N:21]=4)[CH2:16][CH2:15]3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8]([O:13][C@H:14]3[CH2:15][CH2:16][C@H:17]([C:20]4[NH:21][C:22]5[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=5[N:24]=4)[CH2:18][CH2:19]3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8]([O:13][C@@H:14]3[CH2:15][CH2:16][C@H:17]([C:20]4[NH:21][C:22]5[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=5[N:24]=4)[CH2:18][CH2:19]3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

The mixture of 2-{4-[3-(3,6-dihydro-2H-pyran-4-yl)-pyridin-2-yloxy]-cyclohexyl}-1H-benzoimidazole (0.15 g, 0.45 mmol), Pd/C (0.5 g) in MeOH (50 mL) was stirred under H2 atmosphere at 40° C. for 24 h. Then the reaction mixture was filtrated and the filtrate was concentrated and purified by prep-HPLC to give trans-2-{4-[3-(Tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclohexyl}-1H-benzoimidazole (0.11 g, 0.292 mmol, 65% yield) and cis-2-{4-[3-(Tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclohexyl}-1H-benzoimidazole (0.1 g, 0.265 mmol, 60% yield) as white solid. [M+1] 378 each. IC50 (uM): (trans) 0.023 and (cis) 0.025.

Workup

filtrationThen the reaction mixture was filtrated
concentrationthe filtrate was concentrated
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-08e26406f33a448e97e0744fc938ec5e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952037B2

Reaction notes

Loading…