Water → HCID 57415378, 화합물

HRID 68368

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HRID 68368 반응식
C(OC([N:8]([C:12]1[S:13][CH2:14][C@@H:15]2[C@@H:20]([CH3:21])[O:19][CH2:18][C@:16]2([C:22]2[CH:27]=[C:26](Br)[CH:25]=[CH:24][C:23]=2[F:29])[N:17]=1)C([O-])=O)=O)(C)(C)C.O.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[N:37][CH:38]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C([O-])(O)=O.[Na+].Cl[Pd]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[F:29][C:23]1[CH:24]=[CH:25][C:26]([C:35]2[CH:36]=[N:37][CH:38]=[C:33]([C:32]([F:43])([F:42])[F:31])[CH:34]=2)=[CH:27][C:22]=1[C@:16]12[CH2:18][O:19][C@H:20]([CH3:21])[C@H:15]1[CH2:14][S:13][C:12]([NH2:8])=[N:17]2

참가 물질

9

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 45158900[5-(Trifluoromethyl)pyridin-3-yl]boronic acidHCID 86707808tert-Butyl[(4aS,5R,7aS)-7a-(5-bromo-2-fluorophenyl)-5-methyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]imidodicarbonate

생성물 1

HCID 57415378HCID 57415378, 화합물수율 25%

시약·촉매·용매 4

HCID 13169693Triphenylphosphine palladium dichloride촉매HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매HCID 516892Sodium Bicarbonate용매

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온도
100 °C

실험 절차

tert-Butyl[(4aS,5R,7aS)-7a-(5-bromo-2-fluorophenyl)-5-methyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]imidodicarbonate (0.15 g, 0.34 mmol) was dissolved in 1,2-dimethoxyethane (1.5 mL), water (0.7 mL) and ethanol (0.5 mL). The resulting solution was heated to 100° C. and to it was added [5-(trifluoromethyl)pyridin-3-yl]boronic acid (0.32 g, 1.68 mmol), cesium carbonate (0.659 g, 2.02 mmol) and dichloropalladium-triphenylphosphane (0.047 g, 0.067 mmol) and the reaction was stirred at 100° C. After 1 hour, the reaction mixture was cooled to room temperature, diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified using column chromatography (gradient 0-60% EtOAc in hexane). The purified product was dissolved in DCM (2 mL) and trifluoroacetic acid (2 L). After 1 hour, the solvents were removed in vacuo. The residue was neutralised with saturated aqueous NaHCO3 and extracted with DCM (×2). The combined organic layers were dried (MgSO4), filtered and concentrated to give the title compound (35 mg, colourless solid).

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (×3)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. dissolutionThe purified product was dissolved in DCM (2 mL)
  8. waitAfter 1 hour
  9. customthe solvents were removed in vacuo
  10. extractionextracted with DCM (×2)
  11. dry with materialThe combined organic layers were dried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9ce01cdf0d4646c2ad86ada256a3921f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822455B2

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