Trimethylsilylacetylene → 1-(4-Chlorophenyl)-N-[3-ethynyl-4-(4-morpholinopiperidin-1-yl)phenyl]-5-methylpyrazole-4-carboxamide

HRID 1744643노트

반응식

HRID 1744643 반응식
Br[C:2]1[CH:3]=[C:4]([NH:20][C:21]([C:23]2[CH:24]=[N:25][N:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:27]=2[CH3:28])=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1.C[Si]([C:40]#[CH:41])(C)C>N1CCCCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([N:26]2[C:27]([CH3:28])=[C:23]([C:21]([NH:20][C:4]3[CH:5]=[CH:6][C:7]([N:8]4[CH2:13][CH2:12][CH:11]([N:14]5[CH2:19][CH2:18][O:17][CH2:16][CH2:15]5)[CH2:10][CH2:9]4)=[C:2]([C:40]#[CH:41])[CH:3]=3)=[O:22])[CH:24]=[N:25]2)=[CH:30][CH:31]=1

참가 물질

4

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 22227912HCID 22227912, 화합물

생성물 1

HCID 222279551-(4-Chlorophenyl)-N-[3-ethynyl-4-(4-morpholinopiperidin-1-yl)phenyl]-5-methylpyrazole-4-carboxamide수율 3%

시약·촉매·용매 1

HCID 8082Piperidine용매

실험 절차

A suspension of N-[3-bromo-4-(4-morpholinopiperidin-1-yl)phenyl]-1-(4-chlorophenyl)-5-methylpyrazole-4-carboxamide (1 g), bistriphenylphosphinepalladium dichloride (0.38 g), cuprous iodide (0.06 g), trimethylsilylacetylene (0.53 g) and piperidine (50 ml) was refluxed under heating for 15 h. The solvent was evaporated and the residue was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane). The resulting residue was dissolved in methanol (10 ml) and potassium carbonate (170 mg) was added. The mixture was stirred at room temperature for 1 h. After the reaction, potassium carbonate was filtered off. The filtrate was purified by silica gel column chromatography (mobile phase: chloroform/methanol) and recrystallized from a mixed solvent of chloroform-diisopropyl ether to give the title compound (27 mg), melting point: 203–205° C.

후처리

  1. temperaturewas refluxed
  2. temperatureunder heating for 15 h
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane)
  5. dissolutionThe resulting residue was dissolved in methanol (10 ml)
  6. additionpotassium carbonate (170 mg) was added
  7. customAfter the reaction, potassium carbonate
  8. filtrationwas filtered off
  9. customThe filtrate was purified by silica gel column chromatography (mobile phase: chloroform/methanol)
  10. customrecrystallized from a mixed solvent of chloroform-diisopropyl ether

출처 및 근거

ORD 기록
ord-15aab6ffd61e4a128093d67afcee3576
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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