Hydrochloric Acid → 1-(1-hydroxy-2-piperidin-4-ylethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

HRID 1095352ノート

反応式

HRID 1095352 の反応式
[OH:1][CH:2]([C:17]1[N:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:19]=[C:20]2[C:29]=1[C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:22][C:21]2=[O:30])[CH2:3][CH:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1.Cl.[OH-].[Na+]>C(#N)C>[OH:1][CH:2]([C:17]1[N:18]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:19]=[C:20]2[C:29]=1[C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:22][C:21]2=[O:30])[CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57446217HCID 57446217、化合物

生成物 1

HCID 574462181-(1-hydroxy-2-piperidin-4-ylethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one収率 51.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Tert-butyl 4-[2-hydroxy-2-(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate (100 mg, 0.2 mmol) was combined with concentrated hydrochloric acid (1 mL) and stirred at ambient temperature for 30 min. The reaction was poured over ice and the pH of the ice slurry was brought to 12 with 50% aqueous sodium hydroxide. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting material was purified by automated flash chromatography (AnaLogix, eluted with a gradient of 0-60% CMA in chloroform) to provide an oily solid. The oily solid was stirred in acetonitrile. A solid was isolated by filtration to provide 40 mg of 1-(1-hydroxy-2-piperidin-4-ylethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as a tan powder, mp 258-261° C. MS (APCI) m/z 389 (M+H)+; Anal. calcd for C23H24N4O2.0.6H2O: C, 69.19; H, 6.36; N, 14.03. Found: C, 69.02; H, 6.23; N, 14.11.

後処理

  1. additionThe reaction was poured over ice
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting material was purified by automated flash chromatography (AnaLogix
  7. washeluted with a gradient of 0-60% CMA in chloroform)
  8. customto provide an oily solid
  9. customA solid was isolated by filtration

出典と根拠

ORDレコード
ord-5b1cc39b268e44a9844edcc73fd11f7a
出典データセット
uspto-grants-2012_03
特許番号
US08138173B2

反応ノート

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