(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 1880070노트

반응식

HRID 1880070 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

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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-d4b2bed317ae442b80e8eef515469dc7
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318718B2

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