3-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enol → 3-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopentanol

HRID 473666Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:26]=[CH:25][C:11]([O:12][C:13]2[C:18]([C:19]3[CH2:23][CH2:22][CH:21]([OH:24])[CH:20]=3)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:10][CH:9]=1>O1CCCC1.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[C:18]([CH:19]3[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]3)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 3-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enol (190 mg, 0.550 mmol) in Tetrahydrofuran (10 mL) was treated with palladium, 10% wt. on activated carbon (58.5 mg, 0.055 mmol, 0.1 equiv). The reaction mixture was purged with vacuum-hydrogen cycles (3×), and stirred at 23° C. under hydrogen. After 5 h, the reaction was heated to 45° C. After 24 h, the reaction was cooled to 23° C., and filtered through celite. The filter cake was washed with tetrahydrofuran (100 mL), the filtrates combined, concentrated in vacuo, and purified by silica gel chromatography (eluant: 0.5-4% methanol/dichloromethane), affording 3-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopentanol (94 mg, 49% yield). MS (ESI, pos. ion) m/z: 348.1 (M+1). IC50 (uM) 0.010.

Workup

customThe reaction mixture was purged with vacuum-hydrogen cycles (3×)
temperaturethe reaction was heated to 45° C
waitAfter 24 h
temperaturethe reaction was cooled to 23° C.
filtrationfiltered through celite
washThe filter cake was washed with tetrahydrofuran (100 mL)
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluant: 0.5-4% methanol/dichloromethane)

Sources & evidence

ORD record: ord-8f78f67e2c044a6594eba5ad57d246c3
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

Loading…