Ethylenediamine → HCID 2990663, 화합물

HRID 2041183노트

반응식

HRID 2041183 반응식
Br[C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1.[Cu](C#N)[C:19]#[N:20].C(N)CN>CN(C=O)C>[C:19]([C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1)#[N:20]

참가 물질

5

반응물 3

HCID 3301EthylenediamineHCID 90711954-Bromo-N-cyclohexyl-2-fluorobenzamideHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 2990663HCID 2990663, 화합물수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Heat a mixture of 4-bromo-N-cyclohexyl-2-fluoro-benzamide (1.24 g, 4.13 mmol) and copper cyanide (740 mg, 8.26 mmol) in DMF (20 mL) to reflux for 16 h. Cool the mixture to ambient temperature, add aqueous ethylenediamine and stir for 30 min. Extract the mixture with hexane/EtOAc (1:1), dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1) to give the desired intermediate as a white solid (620 mg, 61%). MS (ES−) m/z: 245 (M−H)−.

후처리

  1. temperatureHeat
  2. temperatureto reflux for 16 h
  3. extractionExtract the mixture with hexane/EtOAc (1:1)
  4. dry with materialdry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1)

출처 및 근거

ORD 기록
ord-d7e636df9bde4dad8c4e8fad74972d92
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580780B2

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