Water → HCID 178461595, 화합물

HRID 522814노트

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HRID 522814 반응식
Br[C:2]1[NH:3][C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@H:12]1[CH3:17])[N:7]=[C:6]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][C@H:19]1[CH3:24])[N:5]=2.O.[NH:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[F-].[Cs+]>C(#N)C.C(Cl)Cl.C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31]1[CH:36]=[CH:35][C:34]([C:2]2[NH:3][C:4]3[C:9]([N:10]=2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:7]=[C:6]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@H:19]2[CH3:24])[N:5]=3)=[CH:33][CH:32]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 25953Cesium fluorideHCID 66575043(4-(1H-Imidazol-2-yl)phenyl)boronic acidHCID 178461594HCID 178461594, 화합물

생성물 1

HCID 178461595HCID 178461595, 화합물수율 50.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 3776Isopropanol용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

8-Bromo-2,6-bis-((R)-3-methyl-morpholin-4-yl)-9H-purine (99 mg, 250 μmol) was dissolved in 2 mL of acetonitrile and 0.2 mL of water under argon. 4-(1H-imidazol-2-yl)phenyl boronic acid (58.7 mg, 313 μmol), CsF (57 mg, 375 μmol), and Pd(PPh3)4 (28.9 mg, 25 μmol) were added. The suspension was stirred at 50° C. for 10 minutes in a closed microwave vial. Then it was irradiated for 40 minutes in a microwave apparatus at 150° C. The vial was cooled and uncapped, and the reaction mixture was diluted with 50 mL of CH2Cl2 and 10 mL of isopropanol. The organic solvents were washed with brine and aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (40 g SiO2, CH2Cl2/EtOH/aqueous NH3 in a gradient from 100/0/0.1 to 90/10/0.1) to give the product as a solid (58 mg, 48%).

후처리

  1. customThen it was irradiated for 40 minutes in a microwave apparatus at 150° C
  2. temperatureThe vial was cooled
  3. washThe organic solvents were washed with brine and aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (40 g SiO2, CH2Cl2/EtOH/aqueous NH3 in a gradient from 100/0/0.1 to 90/10/0.1)

출처 및 근거

ORD 기록
ord-6a5c567c6cf84e85a83f7265ee75d0bc
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334271B2

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