(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

HRID 410203노트

반응식

HRID 410203 반응식
[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]

참가 물질

5

반응물 1

HCID 59326884(1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol

생성물 1

HCID 593268581h-Benzimidazol-2-Yl(4-{[3-(Tetrahydro-2h-Pyran-4-Yl)pyridin-2-Yl]oxy}phenyl)methanone

시약·촉매·용매 3

HCID 178418406HCID 178418406, 화합물촉매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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) +++++.

후처리

  1. filtrationthe reaction was filtered
  2. temperaturewhile warm through a small pad of celite
  3. custompurified by column chromatography on silica gel using a gradient of 0 to 10% MeOH
  4. customthe residue was triturated in ethyl ether

출처 및 근거

ORD 기록
ord-235287e2592d4fbdb67aeb25ef9ecb10
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759532B2

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