Triethylamine → HCID 50913358、化合物

HRID 2273574ノート

反応式

HRID 2273574 の反応式
[CH:1]1([C:4]2[C:8]([C:9]([OH:11])=O)=[CH:7][O:6][N:5]=2)[CH2:3][CH2:2]1.S(Cl)(Cl)=O.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.ClCCl>[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:9]([C:8]2[C:4]([CH:1]3[CH2:2][CH2:3]3)=[N:5][O:6][CH:7]=2)=[O:11])[CH:17]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 24386Thionyl ChlorideHCID 450847723-Cyclopropyl-1,2-oxazole-4-carboxylic acid

生成物 1

HCID 50913358HCID 50913358、化合物

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
65 °C

実験手順

400 mg (2.6 mmol) of 3-cyclopropyl-isoxazole-4-carboxylic acid were suspended in 10 mL of toluene and one drop of dimethylformamide was added to the mixture. 0.24 mL of thionylchloride (3.3 mmol) were added at room temperature and the reaction mixture was stirred at 65° C. for two hours. After removal of the solvent, toluene was added and the evaporation was repeated. The obtained residue was then dissolved in 5 mL of dichloromethane and the solution was added dropwise to a solution containing 246 mg pyridin-3-ylamine (2.6 mmol) and 0.45 ml triethyl amine (3.3 mmol) in 5 ml dichloromethane. The mixture was stirred at room temperature for 16 h and the solvent was removed under vacuum. The residue was purified by flash column chromatography (silica, gradient elution cyclohexane→ethyl acetate→methanol) and the solvent was removed under vacuum to give 436 mg (69%, 95% purity) of the title compound as a brown solid.

後処理

  1. customAfter removal of the solvent, toluene
  2. additionwas added
  3. customthe evaporation
  4. dissolutionThe obtained residue was then dissolved in 5 mL of dichloromethane
  5. additionthe solution was added dropwise to a solution
  6. stirringThe mixture was stirred at room temperature for 16 h
  7. customthe solvent was removed under vacuum
  8. customThe residue was purified by flash column chromatography (silica, gradient elution cyclohexane→ethyl acetate→methanol)
  9. customthe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-f8f8674537ee42e1b1cc591479683bb9
出典データセット
uspto-grants-2015_09
特許番号
US09125414B2

反応ノート

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