Potassium Carbonate → HCID 11555326, 화합물

HRID 20537노트

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HRID 20537 반응식
C(=O)([O-])[O-].[K+].[K+].[Si]([O:14][CH2:15][C@H:16]([CH3:36])[O:17][C:18]1[CH:19]=[C:20]([CH:32]=[C:33]([OH:35])[CH:34]=1)[C:21]([NH:23][C:24]1[CH:28]=[CH:27][N:26]([CH:29]([CH3:31])[CH3:30])[N:25]=1)=[O:22])(C(C)(C)C)(C)C.[Cl:37][C:38]1[CH:39]=[C:40]([CH:47]=[CH:48][C:49]=1F)[C:41]([N:43]1[CH2:46][CH2:45][CH2:44]1)=[O:42]>C(#N)C>[N:43]1([C:41]([C:40]2[CH:47]=[CH:48][C:49]([O:35][C:33]3[CH:32]=[C:20]([CH:19]=[C:18]([O:17][C@@H:16]([CH3:36])[CH2:15][OH:14])[CH:34]=3)[C:21]([NH:23][C:24]3[CH:28]=[CH:27][N:26]([CH:29]([CH3:30])[CH3:31])[N:25]=3)=[O:22])=[C:38]([Cl:37])[CH:39]=2)=[O:42])[CH2:46][CH2:45][CH2:44]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 536296483-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-[1-(1-methylethyl)-1H-pyrazol-3-yl]benzamideHCID 59346868(Azetidin-1-yl)(3-chloro-4-fluorophenyl)methanone

생성물 1

HCID 11555326HCID 11555326, 화합물수율 79.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
160 °C

실험 절차

Potassium carbonate (182 mg, 1.32 mmol) was added to a mixture of 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxy-N-(1-isopropyl-1H-pyrazol-3-yl)benzamide (350 mg, 0.81 mmol) and 1-(3-Chloro-4-fluorobenzoyl)azetidine (181 mg, 0.85 mmol) in acetonitrile (5 mL) and the stirred mixture heated at 160° C. in a ‘Smith Creator Microwave’ for 15 hours. The mixture was allowed to reach ambient temperature and pressure and reduced in vacuo. The residual oil was partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate layer was separated, washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (331 mg)

후처리

  1. customto reach ambient temperature
  2. customThe residual oil was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customThe ethyl acetate layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas chromatographed on silica
  8. washeluting with a gradient of 50-100% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-21e1992f9276478baa18bc0885628bbc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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