Water → HCID 59351310, 화합물

HRID 555832노트

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HRID 555832 반응식
[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:17]=[CH:16][C:15]([O:18][C:19]2[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].C([O-])(=O)C.[K+].[CH3:31][O:32][CH:33]1[CH2:38][CH2:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][CH2:34]1.O>CC#N>[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:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:36]3[CH2:37][CH2:38][CH:33]([O:32][CH3:31])[CH2:34][CH:35]=3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

참가 물질

6

반응물 4

HCID 962WaterHCID 517044Potassium AcetateHCID 46207940(4-(3-chloropyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanoneHCID 593514324-Methoxycyclohexene-1-boronic Acid Pinacol Ester

생성물 1

HCID 59351310HCID 59351310, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

(1H-Benzo[d]imidazol-2-yl)(4-(3-chloropyrazin-2-yloxy)phenyl)methanone (1.0 g, 2.8 mmol), potassium acetate (2.1 g, 21.0 mmol), 2-(4-methoxy-1-cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.88 g, 3.7 mmol), and bis[di-tert-butyl(phenyl) phosphane]dichloropalladium (0.13 g, 0.213 mmol) were taken up in 40 mL of 3:1 MeCN:water. The mixture was purged with nitrogen and heated to 100° C. After 12 hours, the mixture was cooled to room temperature and diluted with 40 mL of water. The mixture was extracted twice with 30 mL of 9:1 chloroform:IPA. The combined organic extracts were dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (0.5 to 5% MeOH/DCM) afforded 1H-Benzimidazol-2-yl(4-((3-(4-methoxy-1-cyclohexen-1-yl)-2-pyrazinyl)oxy)phenyl)methanone as a yellow solid. MS (ESI, pos. ion) m/z: 427.1 (M+1). IC50 (uM) +++++.

후처리

  1. customThe mixture was purged with nitrogen
  2. temperaturethe mixture was cooled to room temperature
  3. additiondiluted with 40 mL of water
  4. extractionThe mixture was extracted twice with 30 mL of 9:1 chloroform
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationFiltration and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-2477abdc587c4a9f9a1d3ccf789d36a3
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053438B2

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