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

HRID 1744643ノート

反応式

HRID 1744643 の反応式
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

参加物

4

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 22227912HCID 22227912、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8082Piperidine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15aab6ffd61e4a128093d67afcee3576
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

反応ノート

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