N-methyl-2-pyrrolidone → 3-Benzoyl-7-chloropyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione

HRID 1954747ノート

反応式

HRID 1954747 の反応式
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[C:9]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:10][NH:11][C:12]=2[C:13]([O:15]CC)=O)=[O:7])=[C:4]([NH2:28])[CH:3]=1.CN1CCCC1=O.C([O-])(=O)C.[NH4+]>O>[C:18]([C:9]1[C:8]2[C:6](=[O:7])[C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][C:4]=3[NH:28][C:13](=[O:15])[C:12]=2[NH:11][N:10]=1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 517165Ammonium AcetateHCID 18358872ethyl 4-(4-chloro-2-aminobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate

生成物 1

HCID 183588743-Benzoyl-7-chloropyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione収率 5.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

A solution of ethyl 4-(4-chloro-2-aminobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate (620 mg, 1.56 mmol), 1-methyl-2-pyrrolidinone (4 mL) and ammonium acetate (120 mg, 1.56 mmol) was heated at 146° C. for 16.5 hours. The temperature was increased to 160° C. for 1 hour. The solution was allowed to cool to room temperature and water (60 mL) was added. The insoluble material (468 mg) was filtered, dried, and twice subjected to flash chromatography eluting with hexanes:ethyl acetate (90:10-50:50) to give impure product. The crude solid was triturated with ethanol (15 mL), washed with ethanol (3×10 mL) and dried to give the title compound (30.5 mg, 5.6% yield m.p. 370-373° C. dec.).

後処理

  1. temperatureto cool to room temperature
  2. filtrationThe insoluble material (468 mg) was filtered
  3. customdried
  4. washeluting with hexanes:ethyl acetate (90:10-50:50)
  5. customto give impure product
  6. customThe crude solid was triturated with ethanol (15 mL)
  7. washwashed with ethanol (3×10 mL)
  8. customdried

出典と根拠

ORDレコード
ord-4ac5aee45e584f01a57da96d25272294
出典データセット
uspto-grants-2000_09
特許番号
US06124281

反応ノート

読み込み中…