Hydrochloric Acid → 1-(3,4-dichlorophenyl)-N-(2-morpholinoethyl)-1H-pyrazol-3-amine

HRID 1958883ノート

反応式

HRID 1958883 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=O)[CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CSC.B.O.Cl>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12423031(Dimethyl sulfide)trihydroboronHCID 24743570N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamide

生成物 1

HCID 247435681-(3,4-dichlorophenyl)-N-(2-morpholinoethyl)-1H-pyrazol-3-amine収率 55.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice cooled solution of N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamide (0.1 g, 0.28 mmol) in dry tetrahydrofurane (4 ml), in a dry nitrogen atmosphere, was dropwwise added a 2M solution of borane dimethylsulfide in THF (0.7 ml, 1.4 mmol). The solution was slowly warmed to reflux, refluxed 4 hrs and additionally stirred at room temperature for 16 hrs. The mixture was ice cooled while water (2 ml) and 6M HCl (0.5 ml) cautiously added and, then, refluxed for 2 hrs. Solvents were coevaporated with methanol to dryness in vacuo. The crude residue was partitioned between 10% NaOH aqueous solution and ethyle acetate. The combined organic phases were washed with water, dried over sodium sulphate, filtered and evaporated to dryness yielding 94 mg of crude compound which was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate 50:50 to ethylacetate 100%). 1-(3,4-Dichlorophenyl)-N-(2-morpholinoethyl)-1H-pyrazol-3-amine (53 mg) was obtained as an oil.

後処理

  1. temperatureThe solution was slowly warmed
  2. temperatureto reflux
  3. temperaturerefluxed 4 hrs
  4. additioncautiously added
  5. temperaturerefluxed for 2 hrs
  6. customThe crude residue was partitioned between 10% NaOH aqueous solution and ethyle acetate
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customyielding 94 mg of crude compound which
  12. customwas purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate 50:50 to ethylacetate 100%)

出典と根拠

ORDレコード
ord-7f5cda9e89094557b70f2819bbd10285
出典データセット
uspto-grants-2013_04
特許番号
US08410159B2

反応ノート

読み込み中…