Hydrochloric Acid → HCID 19913634、化合物

HRID 2072776ノート

反応式

HRID 2072776 の反応式
B.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][C:12](=O)[N:11]([CH:16]([CH3:18])[CH3:17])[CH2:10]2)=[CH:5][C:4]=1[C:19]#[N:20].CO.[ClH:23]>O1CCCC1>[ClH:23].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][CH2:12][N:11]([CH:16]([CH3:18])[CH3:17])[CH2:10]2)=[CH:5][C:4]=1[C:19]#[N:20]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 19913626HCID 19913626、化合物

生成物 1

HCID 19913634HCID 19913634、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Borane in tetrahydrofuran (1.0M solution; 7.5 ml) was added dropwise, at ambient temperature, to a stirred solution of 2-[4-amino-3-cyanophenyl]-4-[1-methylethyl]-5-oxomorpholine (0.83 g) in dry tetrahydrofuran (60 ml) under nitrogen. The mixture was then heated under reflux with stirring, under nitrogen, for three hours, cooled and methanol (4 ml) in tetrahydrofuran (10 ml) added carefully. The mixture was heated under reflux for one hour, cooled, hydrogen chloride gas passed and the mixture heated under reflux for one hour. After cooling and evaporation to dryness, the residue was dissolved in dilute hydrochloric acid, washed with diethyl ether, the aqueous phase made alkaline by addition of dilute aqueous sodium hydroxide and extracted with dichloromethane. The dichloromethane extracts were washed with brine, dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated to dryness. The residual oil was purified by chromatography on silica gel using 2-3% methanol in dichloromethane as eluant. Conversion to its hydrochloride salt by addition of ethereal hydrogen chloride and recrystallisation from acetone-diethyl ether gave the title compound, m.p. 200°-2° C., as a white solid.

後処理

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for one hour
  6. temperaturecooled
  7. temperaturethe mixture heated
  8. temperatureunder reflux for one hour
  9. temperatureAfter cooling
  10. customevaporation to dryness
  11. dissolutionthe residue was dissolved in dilute hydrochloric acid
  12. washwashed with diethyl ether
  13. additionby addition of dilute aqueous sodium hydroxide
  14. extractionextracted with dichloromethane
  15. washThe dichloromethane extracts were washed with brine
  16. dry with materialdried over anhydrous magnesium sulphate
  17. filtrationfiltered
  18. customthe filtrate evaporated to dryness
  19. customThe residual oil was purified by chromatography on silica gel using 2-3% methanol in dichloromethane as eluant
  20. additionConversion to its hydrochloride salt by addition of ethereal hydrogen chloride and recrystallisation from acetone-diethyl ether

出典と根拠

ORDレコード
ord-8ad2345c8fe9484b9c405977cf62cd47
出典データセット
uspto-grants-1990_04
特許番号
US04914202

反応ノート

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