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

HRID 1356022

反応式

HRID 1356022 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 185073096-Amino-4-benzylamino-2-furan-2-yl-nicotinonitrile収率 38%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-43d2dd40bb0f4550a44a7c264d7c75bc
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

関連ノート

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