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Ethanamine, 2,2,2-trifluoro- → (R)-Benzyl 4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate

HRID 552567
ノート
印刷プレビュー

反応式

HRID 552567 の反応式
CO[C:3](=[O:29])[C@H:4]([NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:5][C:6]1[C:7]([CH2:16]Cl)=[C:8]2[C:12](=[C:13]([Cl:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2.[F:30][C:31]([F:35])([F:34])[CH2:32][NH2:33].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:22]([O:21][C:19](=[O:20])[NH:18][C@H:4]1[C:3](=[O:29])[N:33]([CH2:32][C:31]([F:35])([F:34])[F:30])[CH2:16][C:7]2[C:8]3[CH:9]=[N:10][NH:11][C:12]=3[C:13]([Cl:15])=[CH:14][C:6]=2[CH2:5]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9773Ethanamine, 2,2,2-trifluoro-2 回HCID 11430Potassium CarbonateHCID 597318592-(R)-benzyloxycarbonylamino-3-(7-chloro-4-chloromethyl-1H-indazol-5-yl)propionic acid methyl ester

生成物 1

HCID 59732091(R)-Benzyl 4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

反応条件

温度
40 °C

実験手順

A mixture of 2-(R)-benzyloxycarbonylamino-3-(7-chloro-4-chloromethyl-1H-indazol-5-yl)propionic acid methyl ester (525 mg, 1.20 mmol) [Chaturvedula et al. WO 2006/052378], trifluoroethylamine (1.0 g, 10.2 mmol), and K2CO3 (499 mg, 3.61 mmol) in CH3CN (15 mL) was heated at 40° C. in a sealed vessel for 45 h. Additional trifluoroethylamine (1.0 g, 10.2 mmol) was added and the mixture was heated at 40° C. for a further 48 h and then allowed to cool to ambient temperature. The reaction mixture was filtered through a 0.45 μm PTFE membrane and the filtrate was concentrated in vacuo. The residue was dissolved in toluene (10 mL) and AcOH (1 mL) and the mixture was heated at reflux for 6 h, allowed to cool to ambient temperature, and partitioned between saturated aqueous NaHCO3 (30 mL) and EtOAc (60 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc-100:0 to 50:50, to provide the title compound. MS: m/z=467.

後処理

  1. temperaturethe mixture was heated at 40° C. for a further 48 h
  2. temperatureto cool to ambient temperature
  3. filtrationThe reaction mixture was filtered through a 0.45 μm PTFE membrane
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in toluene (10 mL)
  6. temperatureAcOH (1 mL) and the mixture was heated
  7. temperatureat reflux for 6 h
  8. temperatureto cool to ambient temperature
  9. custompartitioned between saturated aqueous NaHCO3 (30 mL) and EtOAc (60 mL)
  10. washThe organic layer was washed with brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe crude product was purified by silica gel chromatography
  15. washeluting with a gradient of CH2Cl2

出典と根拠

ORDレコード
ord-1c2700b4efae4ada9b28da4d7bb93927
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951795B2

反応ノート

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