Sodium Carbonate → N-[5-[1-Methyl-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide

HRID 38870

반응식

HRID 38870 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([C:12]2[O:13][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]3)=[N:15][N:16]=2)[CH:3]=1.[CH3:27][O:28][C:29]1[C:34]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[CH3:11][N:8]1[C:9]2[C:5](=[C:4]([C:12]3[O:13][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]4)=[N:15][N:16]=3)[CH:3]=[C:2]([C:32]3[CH:33]=[C:34]([NH:35][S:36]([CH3:39])(=[O:37])=[O:38])[C:29]([O:28][CH3:27])=[N:30][CH:31]=3)[CH:10]=2)[CH:6]=[N:7]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 59564698N-(2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methanesulfonamideHCID 666958946-Bromo-1-methyl-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazole

생성물 1

HCID 46917599N-[5-[1-Methyl-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide수율 38.9%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

6-Bromo-1-methyl-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazole (40 mg, 0.095 mmol), N-[2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methanesulfonamide (31.3 mg, 0.095 mmol), sodium carbonate (30.3 mg, 0.286 mmol) and 1,1-bis(diphenylphosphino)ferrocene palladium dichloride (6.98 mg, 9.54 μmol) were added to a microwave vial and dissolved in 1,4-dioxane (0.5 ml) and water (0.5 ml). The reaction mixture was heated under microwave irradiation at 110° C. for 15 mins. The reaction mixture was evaporated under a stream of nitrogen and the residual solid was dissolved in DMSO (1 ml), filtered through a frit and purified by Mass Directed Automated Preparative HPLC (Method B). The solvent was evaporated under a stream of nitrogen and the residue was dissolved in 1,4-dioxane (1 ml) and water (1 ml), frozen in a cardice bath and placed on the freeze-drier for 18 h to afford the title compound as a white solid (20 mg).

후처리

  1. customThe reaction mixture was evaporated under a stream of nitrogen
  2. dissolutionthe residual solid was dissolved in DMSO (1 ml)
  3. filtrationfiltered through a frit
  4. custompurified by Mass Directed Automated Preparative HPLC (Method B)
  5. customThe solvent was evaporated under a stream of nitrogen
  6. dissolutionthe residue was dissolved in 1,4-dioxane (1 ml)
  7. temperaturewater (1 ml), frozen in a cardice bath

출처 및 근거

ORD 기록
ord-bc09b36d4fe04f579cdba4774a41f8b2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524751B2

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