Citric Acid → 4-Amino-5-Cyano-2-fluoro-6-methylbiphenyl-3-yl cyclobutanecarboxylate

HRID 17498

反応式

HRID 17498 の反応式
[NH2:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH3:18])[C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[CH:26]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][CH2:27]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C>[CH:26]1([C:30]([O:10][C:9]2[C:8]([F:11])=[C:7]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]([CH3:18])=[C:3]([C:4]#[N:5])[C:2]=2[NH2:1])=[O:31])[CH2:29][CH2:28][CH2:27]1

参加物

6

反応物 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

生成物 1

HCID 866308594-Amino-5-Cyano-2-fluoro-6-methylbiphenyl-3-yl cyclobutanecarboxylate収率 85%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

Under nitrogen atmosphere, 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (250 mg, 1.03 mmol) was dissolved in acetonitrile (0.10 ml), and cooled to 0° C. Triethylamine (244 μl, 1.75 mmol) and cyclobutanecarbonyl chloride (177 μl, 1.55 mmol) were dropwise added to the solution, followed by stirring at room temperature for 1 hour. 10% citric acid was added to the reaction liquid, and the solvent was evaporated away under, reduced pressure. Ethyl acetate was added to the resulting residue, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate/hexane (1:4, v/v) gave the entitled compound (283 mg, 85%) as a white solid.

後処理

  1. customthe solvent was evaporated away under, reduced pressure
  2. additionEthyl acetate was added to the resulting residue
  3. washby washing with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated away under reduced pressure

出典と根拠

ORDレコード
ord-6306fbf97e3d4cb984eb4bec6402c498
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

読み込み中…