Potassium Carbonate → HCID 11555326、化合物

HRID 20537ノート

反応式

HRID 20537 の反応式
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

参加物

5

反応物 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

生成物 1

HCID 11555326HCID 11555326、化合物収率 79.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
160 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-21e1992f9276478baa18bc0885628bbc
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

読み込み中…