Triethylamine → HCID 178522056、化合物

HRID 45814

反応式

HRID 45814 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:3][CH:2]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1.C(N(CC)CC)C>N1C=CC=CC=1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH:18][C:28]([NH:27][C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:26][CH:25]=4)=[O:29])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 178507541HCID 178507541、化合物

生成物 1

HCID 178522056HCID 178522056、化合物収率 75%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To 3-(4-Pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (700 mg, 3 mmol) in anhydrous pyridine (15 mL) at 0° C. 4-trifluoromethylphenylisocyanate (420 μL, 3 mmol) was added. The reaction was stirred for 2 hours at 0° C. under nitrogen atmosphere to give a mixture of monourea and bis-urea as regioisomeric mixture. Solvent was removed under reduced pressure. The residue was dissolved in methanol (15 mL) and triethylamine (1 mL, 7.8 mmol) was added and the reaction was stirred at room temperature overnight. After this time only the monourea could be detected by HPLC/MS. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL) and washed successively with water (3×50 mL). The crude was purified by silica gel column chromatography (DCM/methanol 9:1) to give the desired product as a white solid (75%).

後処理

  1. customat 0° C
  2. customto give
  3. customSolvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (15 mL)
  5. stirringthe reaction was stirred at room temperature overnight
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  8. washwashed successively with water (3×50 mL)
  9. customThe crude was purified by silica gel column chromatography (DCM/methanol 9:1)

出典と根拠

ORDレコード
ord-568357e338334b369eb32b7a7405ce38
出典データセット
uspto-grants-2013_09
特許番号
US08541575B2

関連ノート

読み込み中…