(1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol → 1h-Benzimidazol-2-Yl(4-{[3-(Tetrahydro-2h-Pyran-4-Yl)pyridin-2-Yl]oxy}phenyl)methanone
反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)[OH:11]>C(Cl)(Cl)Cl.C1COCC1.[O-2].[O-2].[Mn+4]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[C:24]([CH:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:17]=1)=[O:11]参加物
反応物 1
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 50 °C
実験手順
A suspension of (1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol (0.500 g, 1.245 mmol) in Chloroform (50 mL) and THF (50.0 mL) was treated with manganese dioxide (1.083 g, 12.45 mmol) at RT under nitrogen. The mixture was heated to 50° C. while stirring. After 40 mins, the reaction was filtered while warm through a small pad of celite. The filtrate was reduced and purified by column chromatography on silica gel using a gradient of 0 to 10% MeOH is DCM. The pure fractions were reduced and the residue was triturated in ethyl ether to give (1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone as an off-white solid. MS (ESI, pos. ion) m/z: 399.9 (M+1). IC50 (uM) +++++.
後処理
- filtrationthe reaction was filtered
- temperaturewhile warm through a small pad of celite
- custompurified by column chromatography on silica gel using a gradient of 0 to 10% MeOH
- customthe residue was triturated in ethyl ether
出典と根拠
- ORDレコード
- ord-d4b2bed317ae442b80e8eef515469dc7
- 出典データセット
- uspto-grants-2012_11
- 特許番号
- US08318718B2
反応ノート
読み込み中…