Benzylamine → 6-Amino-4-benzylamino-2-furan-2-yl-nicotinonitrile

HRID 1356022

반응식

HRID 1356022 반응식
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>COCCOC>[NH2:1][C:2]1[CH:3]=[C:4]([NH:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

참가 물질

4

반응물 2

HCID 7504BenzylamineHCID 86583754Trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester

생성물 1

HCID 185073096-Amino-4-benzylamino-2-furan-2-yl-nicotinonitrile수율 38%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 250 mg (0.75 mmol) trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester in 10 ml DME was added 0.82 ml (7.56 mmol) benzylamine and the mixture heated at 80° C. for 72 hours. The reaction mixture was then cooled to room temperature and partitioned between dichloromethane and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether/hexane to afford 79 mg (38%) 6-amino-4-benzylamino-2-furan-2-yl-nicotinonitrile as a white crystalline solid. ES-MS m/e (%): 291 (M+H+, 100).

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between dichloromethane and water
  3. customThe phases were separated
  4. dry with materialthe organic phase dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in ether/hexane

출처 및 근거

ORD 기록
ord-43d2dd40bb0f4550a44a7c264d7c75bc
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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